Method for making photochromic contact lenses

ABSTRACT

Described herein is a method for producing a contact lens comprising a central photochromic zone that has a diameter of about 13 mm or less and is concentric with the central axis of the contact lens. The method comprises: applying a first polymerizable fluid composition containing at least one photochromic compound on a central portion of the molding surface of a female mold half to form a circular layer; partially photocuring, in situ, the circular layer in the female mold half by using a visible light; dispensing a second polymerizable fluid composition over the partially-cured circular layer on the molding surface of the female mold half; and a step of thermally curing the second polymerizable fluid composition and the partially-cured circular layer immersed therein in the mold cavity formed between the the molding surfaces of the female mold half and a male mold half.

This application claims the benefits under 35 USC § 119 (e) of U.S.provisional application Nos. 63/158,064 and 63/158,071, both filed on 8Mar. 2021, incorporated by references in their entireties.

This invention is related to a method for producing contact lenses, inparticular, silicone hydrogel contact lenses, having a centralphotochromic zone. This invention also provides contact lenses madeaccording to a method of the invention.

BACKGROUND

Conventionally, UV-absorbing compounds have been incorporated intocontact lenses to make UV-absorbing contact lenses to protect eyes fromUV-radiations. Recently, there have been proposed various photochromiccontact lenses for protecting eyes from UV-radiations (see, e.g., U.S.Pat. Nos. 4,681,412, 6,017,121, 6,174,464, 6,224,945, 7,261,844,7,368,072, 7,556,750, 7,560,056, 7,584,630, 7,641,337, 7,999,989,8,158,037, 8,697,770, 8,741,188, 9,052,438, 9,097,916, 9,377,569,9,465,234, 9,904,074, 10,197,707). Those proposed photochromic contactlenses contains photochromic compounds which are capable of undergoing areversible color change, e.g., from “clear” to blue or other color, uponexposure to UV/HEVL radiation.

Typically, photochromic contact lenses can be obtained by adding aphotochromic compound in a polymerizable composition (i.e., lensformulation) for forming the contact lenses and then by curing thepolymerizable composition in contact lens molds according to acast-molding lens manufacturing process. A conventional cast-moldinglens manufacturing process comprises: one single-step curing(polymerizing) of one single polymerizable composition (lensformulation) within disposable plastic molds typically consisting of twosingle-use mold halves; opening molds; optionally but preferablydelensing (i.e., removing cast-molded lenses from the molds); and beingsubjected to various post-molding processes including extraction,hydration, packaging, and sterilization, etc.

However, photochromic contact lenses obtained according to such aconventional cast-molding process have photochromic compoundincorporated uniformly within the polymer matrix of the photochromiccontact lenses and are, from edge-to-edge, capable of undergoing areversible color change upon exposure to UV/HEVL-radiation. Suchphotochromic contact lenses are not desirable for cosmetic reasons. Itwould be desirable to produce a photochromic contact lens that changescolor only in the central pupil region.

U.S. Pat. Nos. 7,368,072, 7,560,056, 8,697,770 and 9,904,074 disclosemethods for making photochromic contact lenses only the centralpupillary regions of which can undergo a reversible color change uponexposure to UV/HEVL-radiation. Those methods comprise steps of: dosing aphotochromic lens-forming composition onto the central region of themolding surface of a mold half and followed by adding a clearlens-forming composition on the top of the photochromic lens-formingcomposition, wherein the photochromic lens-forming composition has aviscosity much higher than the clear lens-forming composition; matingwith the other mold half to form a cavity with the photochromic andclear lens-forming compositions therewithin; and curing the photochromicand clear lens-forming compositions within the cavity of the mold toform the photochromic contact lens. However, handling and dosing of ahigh viscous photochromic lens-forming composition could be challengingin a production environment.

Therefore, there is still a need for a method for making photochromiccontact lenses only the central pupillary regions of which can undergo areversible color change upon exposure to UV/HEVL-radiation.

SUMMARY

The invention, in some aspects, provides a method for producing hydrogelcontact lenses, comprising the steps of: (1) obtain a firstpolymerizable fluid composition and a second polymerizable fluidcomposition, wherein the first polymerizable fluid composition comprisesat least one visible-light free-radical photoinitiator, at least onethermal free-radical initiator, at least one first polymerizablematerial, and at least one photochromic compound, wherein the secondpolymerizable fluid composition comprises said at least one thermalfree-radical initiator and at least one second polymerizable materialand is free of any photochromic compound, wherein the firstpolymerizable fluid composition has a curing time as determined inphoto-rheology study using a visible light at a specified intensity; (2)obtaining a lens mold, wherein the lens mold comprises a female moldhalf having a first molding surface defining the anterior surface of acontact lens to be molded and a male mold half having a second moldingsurface defining the posterior surface of the contact lens to be molded,wherein the female and male mold halves are configured to receive eachother such that a mold cavity is formed between the first and secondmolding surfaces when the mold is closed; (3) applying an amount of thefirst polymerizable fluid composition onto a central zone of the firstmolding of the female mold half to form a circular layer of the firstpolymerizable fluid composition, wherein the circular layer has adiameter of about 13.00 mm or less; (4) actinically curing the circularlayer of the first polymerizable fluid composition to form a disk havingcurved surfaces, wherein the step of actinically curing is carried outby irradiating the circular layer of the first polymerizable fluidcomposition with the visible light at the specified intensity for atleast 30% of the curing time; (5) dispensing an amount of the secondpolymerizable fluid composition over the disk on the first moldingsurface; (6) closing the female mold half with the male mold half toform a molding assembly comprising the disk immersed in the secondpolymerizable fluid composition within the mold cavity; (7) thermallycuring the second polymerizable fluid composition with the disk immersedtherein in the molding assembly to form an unprocessed hydrogel contactlens having a central photochromic zone that has a diameter of about 13mm or less, is concentric with the central axis of the unprocessedhydrogel contact lens; (8) separating the molding assembly into the maleand female mold halves, with the unprocessed hydrogel contact lensadhered onto a lens-adhered mold half which is one of the male andfemale mold halves; (9) removing the unprocessed hydrogel contact lensfrom the lens-adhered mold half; and (10) subjecting the unprocessedhydrogel contact lens to post-molding processes including a hydrationprocess and one or more other processes selected from the groupconsisting of extraction, surface treatment, packaging, sterilization,and combinations thereof.

The invention, in other aspects, provides contact lenses producedaccording to a method of the invention

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 schematically illustrates a hydrogel contact lens according to apreferred embodiment of the invention.

FIG. 2 shows a photo-rheology study of a polymerizable composition(Formulation 2A).

DETAILED DESCRIPTION

Unless defined otherwise, all technical and scientific terms used hereinhave the same meaning as commonly understood by one of ordinary skill inthe art to which this invention belongs. Generally, the nomenclatureused herein and the laboratory procedures are well known and commonlyemployed in the art. Conventional methods are used for these procedures,such as those provided in the art and various general references. Wherea term is provided in the singular, the inventors also contemplate theplural of that term. The nomenclature used herein and the laboratoryprocedures described below are those well known and commonly employed inthe art.

“About” as used herein means that a number referred to as “about”comprises the recited number plus or minus 1-10% of that recited number.

“Optional” or “optionally” means that the subsequently described eventor circumstance can or cannot occur, and that the description includesinstances where the event or circumstance occurs and instances where itdoes not.

“Contact Lens” refers to a structure that can be placed on or within awearer's eye. A contact lens can correct, improve, or alter a user'seyesight, but that need not be the case. A contact lens can be of anyappropriate material known in the art or later developed, and can be asoft lens, a hard lens, or a hybrid lens.

A “hydrogel contact lens” refers to a contact lens comprising a hydrogelbulk (core) material. A hydrogel bulk material can be a non-siliconehydrogel material or preferably a silicone hydrogel (SiHy) material.

A “hydrogel” or “hydrogel material” refers to a crosslinked polymericmaterial which has three-dimensional polymer networks (i.e., polymermatrix), is insoluble in water, but can hold at least 10% by weight ofwater in its polymer matrix when it is fully hydrated (or equilibrated).

A “silicone hydrogel” or “SiHy” refers to a silicone-containing hydrogelobtained by copolymerization of a polymerizable composition comprisingat least one silicone-containing vinylic monomer and/or at least onesilicone-containing vinylic crosslinker.

A “siloxane” or “silicone”, as known to a person skilled in the art,interchangeably refers to a moiety of —Si—O—Si— where each Si atomcarries at least two substituents (organic groups) or a molecule havingat least one moiety of —Si—O—Si—.

As used in this application, the term “non-silicone hydrogel” refers toa hydrogel that is theoretically free of silicon.

“Hydrophilic,” as used herein, describes a material or portion thereofthat will more readily associate with water than with lipids.

A “vinylic monomer” refers to a compound that has one sole ethylenicallyunsaturated group, is soluble in a solvent, and can be polymerizedactinically or thermally.

The term “soluble”, in reference to a compound or material in a solvent,means that the compound or material can be dissolved in the solvent togive a solution with a concentration of at least about 0.5% by weight atroom temperature (i.e., a temperature of about 22° C. to about 26° C.).

The term “insoluble”, in reference to a compound or material in asolvent, means that the compound or material can be dissolved in thesolvent to give a solution with a concentration of less than 0.01% byweight at room temperature (as defined above).

The term “ethylenically unsaturated group” is employed herein in a broadsense and is intended to encompass any groups containing at leastone >C═C<group. Exemplary ethylenically unsaturated groups includewithout limitation (meth)acryloyl

and/or

allyl, vinyl, styrenyl, or other C═C containing groups.

As used herein, “actinically” in reference to curing, crosslinking orpolymerizing of a polymerizable composition, a prepolymer or a materialmeans that the curing (e.g., crosslinked and/or polymerized) isperformed by actinic irradiation, e.g., UV/visible light irradiation, orthe like. Thermal curing or actinic curing methods are well-known to aperson skilled in the art.

An “acrylic monomer” refers to a vinylic monomer having one sole(meth)acryloyl group. Examples of acrylic monomers includes(meth)acryloxy [or (meth)acryloyloxy] monomers and (meth)acrylamidomonomers.

An “(meth)acryloxy monomer” or “(meth)acryloyloxy monomer” refers to avinylic monomer having one sole group of

An “(meth)acrylamido monomer” refers to a vinylic monomer having onesole group of

in which R^(o) is H or C₁-C₄ alkyl.

The term “(meth)acrylamide” refers to methacrylamide and/or acrylamide.

The term “(meth)acrylate” refers to methacrylate and/or acrylate.

An “N-vinyl amide monomer” refers to an amide compound having a vinylgroup (—CH═CH₂) that is directly attached to the nitrogen atom of theamide group.

An “ene monomer” refers to a vinylic monomer having one sole ene group.

A “hydrophilic vinylic monomer”, a “hydrophilic acrylic monomer”, a“hydrophilic (meth)acryloxy monomer”, or a “hydrophilic (meth)acrylamidomonomer”, as used herein, respectively refers to a vinylic monomer, anacrylic monomer, a (meth)acryloxy monomer, or a (meth)acrylamidomonomer), which typically yields a homopolymer that is water-soluble orcan absorb at least 10 percent by weight of water.

A “hydrophobic vinylic monomer”, a “hydrophobic acrylic monomer”, a“hydrophobic (meth)acryloxy monomer”, or a “hydrophobic (meth)acrylamidomonomer”, as used herein, respectively refers to a vinylic monomer, anacrylic monomer, a (meth)acryloxy monomer, or a (meth)acrylamidomonomer), which typically yields a homopolymer that is insoluble inwater and can absorb less than 10% by weight of water.

As used in this application, the term “vinylic crosslinker” refers to anorganic compound having at least two ethylenically unsaturated groups. A“vinylic crosslinking agent” refers to a vinylic crosslinker having amolecular weight of 700 Daltons or less.

A “polysiloxane segment” or “polydiorganosiloxane segment”interchangeably refers to a polymer chain segment (i.e., a divalentradical) of

in which SN is an integer of 3 or larger and each of R_(S1) and R_(S2)independent of one another are selected from the group consisting of:C₁-C₁₀ alkyl; phenyl; C₁-C₄-alkyl-substituted phenyl;C₁-C₄-alkoxy-substituted phenyl; phenyl-C₁-C₆-alkyl; C₁-C₁₀ fluoroalkyl;C₁-C₁₀ fluoroether; aryl; aryl C₁-C₁₈ alkyl; -alk-(OC₂H₄)_(γ1)—OR^(o)(in which alk is C₁-C₆ alkylene diradical, R^(o) is H or C₁-C₄ alkyl andγ1 is an integer from 1 to 10); a C₂-C₄₀ organic radical having at leastone functional group selected from the group consisting of hydroxylgroup (—OH), carboxyl group (—COOH), amino linkages of —NR_(N1)—, amidelinkages of —CONR_(N1)—, amide of —CONR_(N1)R_(N1)′, urethane linkagesof —OCONH—, and C₁-C₄ alkoxy group, or a linear hydrophilic polymerchain, in which R_(N1) and R_(N1)′ independent of each other arehydrogen or a C₁-C₁₅ alkyl.

A “polydiorganosiloxane vinylic crosslinker” or “polysiloxane vinyliccrosslinker” interchangeably refers to a compound comprising at leastone polysiloxane segment and at least two ethylenically-unsaturatedgroups.

A “linear polydiorganosiloxane vinylic crosslinker” or “linearpolysiloxane vinylic crosslinker” interchangeably refers to a compoundcomprising a main chain which includes at least one polysiloxane segmentand is terminated with one ethylenically-unsaturated group at each ofthe two ends of the main chain.

A “chain-extended polydiorganosiloxane vinylic crosslinker” or“chain-extended polysiloxane vinylic crosslinker” interchangeably refersto a compound comprising at least two ethylenically-unsaturated groupsand at least two polysiloxane segments each pair of which are linked byone divalent radical.

The term “photochromic vinylic monomer” refers to a vinylic monomer thathas one colorless (or light-colored) form and one colored form and canundergo reversible change from the colorless form (or light-coloredform) (or so-called “deactivated form” to the colored form (or so-called“activated form”) upon exposure to UV/HEVL radiation.

The term “colorless or light-colored stated” or “inactivated state” inreference to a photochromic contact lens means the original state of thephotochromic contact lens before the photochromic contact lens isirradiated with UV/HEVL light. In this state, the photochromic contactlens typically is colorless or shows a faint color as observed by anaked eye.

The term “colored stated” or “activated state” in reference to aphotochromic contact lens means a state of the photochromic contact lenswhen the photochromic contact lens is being irradiated with UV/HEVLlight. In this state, the photochromic contact lens typically shows adark color as observed by a naked eye.

The term “fluid” as used herein indicates that a material is capable offlowing like a liquid.

As used in this application, the term “clear” in reference to apolymerizable composition means that the polymerizable composition is atransparent solution or liquid mixture having a light transmissibilityof 85% or greater (preferably 90% or greater) in the range between 400nm to 700 nm.

A free radical initiator can be either a photoinitiator or a thermalinitiator. A “photoinitiator” refers to a chemical that initiates freeradical crosslinking/polymerizing reaction by the use of UV and/orvisible light. A “thermal initiator” refers to a chemical that initiatesradical crosslinking/polymerizing reaction by the use of heat energy.

The term “acyl germanium photoinitiator” refers to an organogermaniumcompound that is a germanium-based Norrish Type I photoinitiator andcomprises at least one acrylcarbonyl group connected to germanium.Examples of such acyl germanium photoinitiators are described in U.S.Pat. Nos. 7,605,190 and 10,324,311.

As used in this application, the term “polymer” means a material formedby polymerizing/crosslinking one or more monomers or macromers orprepolymers or combinations thereof.

A “macromer” or “prepolymer” refers to a compound or polymer thatcontains ethylenically unsaturated groups and has a number averagemolecular weight of greater than 700 Daltons.

As used in this application, the term “molecular weight” of a polymericmaterial (including monomeric or macromeric materials) refers to thenumber-average molecular weight unless otherwise specifically noted orunless testing conditions indicate otherwise. A skilled person knows howto determine the molecular weight of a polymer according to knownmethods, e.g., GPC (gel permeation chromatochraphy) with one or more ofa refractive index detector, a low-angle laser light scatteringdetector, a multi-angle laser light scattering detector, a differentialviscometry detector, a UV detector, and an infrared (IR) detector;MALDI-TOF MS (matrix-assisted desorption/ionization time-of-flight massspectroscopy); ¹H NMR (Proton nuclear magnetic resonance) spectroscopy,etc.

The term “monovalent radical” refers to an organic radical that isobtained by removing a hydrogen atom from an organic compound and thatforms one bond with one other group in an organic compound. Examplesinclude without limitation, alkyl (by removal of a hydrogen atom from analkane), alkoxy (or alkoxyl) (by removal of one hydrogen atom from thehydroxyl group of an alkyl alcohol), thiyl (by removal of one hydrogenatom from the thiol group of an alkylthiol), cycloalkyl (by removal of ahydrogen atom from a cycloalkane), cycloheteroalkyl (by removal of ahydrogen atom from a cycloheteroalkane), aryl (by removal of a hydrogenatom from an aromatic ring of the aromatic hydrocarbon), heteroaryl (byremoval of a hydrogen atom from any ring atom), amino (by removal of onehydrogel atom from an amine), etc.

The term “divalent radical” refers to an organic radical that isobtained by removing two hydrogen atoms from an organic compound andthat forms two bonds with other two groups in an organic compound. Forexample, an alkylene divalent radical (i.e., alkylenyl) is obtained byremoval of two hydrogen atoms from an alkane, a cycloalkylene divalentradical (i.e., cycloalkylenyl) is obtained by removal of two hydrogenatoms from the cyclic ring.

In this application, the term “substituted” in reference to an alkyl oran alkylenyl means that the alkyl or the alkylenyl comprises at leastone substituent which replaces one hydrogen atom of the alkyl or thealkylenyl and is selected from the group consisting of hydroxyl (—OH),carboxyl (—COOH), —NH₂, sulfhydryl (—SH), C₁-C₄ alkyl, C₁-C₄ alkoxy,C₁-C₄ alkylthio (alkyl sulfide), C₁-C₄ acylamino, C₁-C₄ alkylamino,di-C₁-C₄ alkylamino, and combinations thereof.

The term “terminal ethylenically-unsaturated group” refers to oneethylenically-unsaturated group at one of the two ends of the main chain(or backbone) of an organic compound as known to a person skilled in theart.

A “blending vinylic monomer” refers to a vinylic monomer capable ofdissolving both hydrophilic and hydrophobic components of apolymerizable composition to form a solution.

“Post-curing surface treatment”, in reference to a SiHy contact lens,means a surface treatment process that is performed after the SiHycontact lens is formed by curing (i.e., thermally or actinicallypolymerizing) a SiHy lens formulation.

The term “silicone hydrogel lens formulation” or “SiHy lens formulation”interchangeably refers to a polymerizable composition that comprises allnecessary polymerizable components for producing a SiHy contact lens ora SiHy material as well known to a person skilled in the art.

A “UV-absorbing vinylic monomer” refers to a compound comprising anethylenically-unsaturated group and a UV-absorbing moiety which canabsorb or screen out UV radiation in the range from 200 nm to 400 nm asunderstood by a person skilled in the art.

A “HEVL-absorbing vinylic monomer” refers to a compound comprising anethylenically-unsaturated group and a HEVL-absorbing moiety which canabsorb or screen out HEVL (high-energy-violet-light) radiation in therange from 380 nm to 440 nm as understood by a person skilled in theart.

“UVA” refers to radiation occurring at wavelengths between 315 and 380nanometers; “UVB” refers to radiation occurring between 280 and 315nanometers; “Violet” refers to radiation occurring at wavelengthsbetween 380 and 440 nanometers.

“UVA transmittance” (or “UVA % T”), “UVB transmittance” or “UVB % T”,and “violet-transmittance” or “Violet % T” are calculated by thefollowing formula.

UVA % T=Average % Transmission between 315 nm and 380 nm×100

UVB % T=Average % Transmission between 280 nm and 315 nm×100

Violet % T=Average % Transmission between 380 nm and 440 nm×100

The intrinsic “oxygen permeability”, Dk_(i), of a material is the rateat which oxygen will pass through a material. As used in thisapplication, the term “oxygen permeability (Dk)” in reference to ahydrogel (silicone or non-silicone) or a contact lens means a corectedoxygen permeability (Dk_(c)) which is measured at about 34-35° C. andcorrected for the surface resistance to oxygen flux caused by theboundary layer effect according to the procedures described in ISO18369-4. Oxygen permeability is conventionally expressed in units ofbarrers, where “barrer” is defined as [(cm³ oxygen)(cm)/(cm²)(sec)(mmHg)]×10⁻⁹.

The “oxygen transmissibility”, Dk/t, of a lens or material is the rateat which oxygen will pass through a specific lens or material with anaverage thickness of t [in units of mm] over the area being measured.Oxygen transmissibility is conventionally expressed in units ofbarrers/mm, where “barrers/mm” is defined as [(cm³ oxygen)/(cm²)(sec)(mmHg)]×10-9.

The term “modulus” or “elastic modulus” in reference to a contact lensor a material means the tensile modulus or Young's modulus which is ameasure of the stiffness of a contact lens or a material in tension. Aperson skilled in the art knows well how to determine the elasticmodulus of a SiHy material or a contact lens. For example, allcommercial contact lenses have reported values of elastic modulus.

An “unprocessed state” refers to a contact lens which is obtained bycast-molding of a polymerizable composition in a mold and has not beensubjected to extraction and/or hydration post-molding processes (i.e.,having not been in contact with water or any organic solvent or anyliquid after molding).

A “male mold half” or “base curve mold half” interchangeably refers to amold half having a molding surface that is a substantially convexsurface and that defines the posterior surface of a contact lens.

A “female mold half” or “front curve mold half” interchangeably refersto a mold half having a molding surface that is a substantially concavesurface and that defines the anterior surface of a contact lens.

The term “anterior surface”, “front surface”, “front curve surface” or“FC surface” in reference to a contact lens, as used in thisapplication, interchangeably means a surface of the contact lens thatfaces away from the eye during wear. The anterior surface (frontsurface) is typically substantially convex.

The “posterior surface”, “back surface”, “base curve surface” or “BCsurface” in reference to a contact lens, as used in this application,interchangeably means a surface of the contact lens or insert that facestowards the eye during wear. The posterior surface (back surface) istypically substantially concave.

A “coating” in reference to a contact lens means that the contact lenshas, on its surfaces, a thin layer of a material that is different fromthe bulk material of the contact lens and obtained by subjecting thecontact lens to a surface treatment.

“Surface modification” or “surface treatment”, as used herein, meansthat an article has been treated in a surface treatment process, inwhich (1) a coating is applied to the surface of the article, (2)chemical species are adsorbed onto the surface of the article, (3) thechemical nature (e.g., electrostatic charge) of chemical groups on thesurface of the article are altered, or (4) the surface properties of thearticle are otherwise modified. Exemplary surface treatment processesinclude, but are not limited to, a surface treatment by energy (e.g., aplasma, a static electrical charge, radiation, or other energy source),chemical treatments, the grafting of hydrophilic vinylic monomers ormacromers onto the surface of an article, mold-transfer coating processdisclosed in U.S. Pat. No. 6,719,929, the incorporation of wettingagents into a lens formulation for making contact lenses proposed inU.S. Pat. Nos. 6,367,929 and 6,822,016, reinforced mold-transfer coatingdisclosed in U.S. Pat. No. 7,858,000, and a hydrophilic coating composedof covalent attachment or physical deposition of one or more layers ofone or more hydrophilic polymer onto the surface of a contact lensdisclosed in U.S. Pat. Nos. 8,147,897, 8,409,599, 8,557,334, 8,529,057,and 9,505,184.

A “hydrophilic surface” in reference to a material or a contact lensmeans that the material or the contact lens has a surface hydrophilicitycharacterized by having an averaged water contact angle of about 90degrees or less, preferably about 80 degrees or less, more preferablyabout 70 degrees or less, more preferably about 60 degrees or less.

An “average contact angle” refers to a water contact angle (static watercontact angle measured by Sessile Drop), which is obtained by averagingmeasurements of at least 3 individual contact lenses.

The term “central axis” in reference to a contact lens means a linepassing through the geometrical centers of the anterior and posteriorsurfaces of the contact lens.

In general, the invention is directed to a method for making contactlenses, in particular, SiHy contact lenses, each of which comprises acentral photochromic zone that has a diameter of about 13 mm or less andis concentric with the central axis of the contact lens.

FIG. 1 schematically illustrates a contact lens of the invention. Thecontact lens 100 has an aterior surface 102, an opposite posteriorsurface, a central axis 101, and a central zone 110 that has a diameter120 and is concentric with the central axis 101 of the contact lens 100.The central zone 110 comprises at least one photochromic compound thatis distributed in its front portion 112 (a portion near and including acentral portion of the anterior surface) and provides the photochromicfunctionality to the central zone.

The invention is partly based on the discovery that such contact lensescan be produced according to a process involving: a first step ofdosing—applying a small amount of a first polymerizable fluidcomposition, which comprises at least one polymerizable photochromiccompound and a visible-light free-radical photoinitiator as well as athermal free-radical initiator, on a central portion of the moldingsurface of a female mold half to form a circular layer of the firstpolymerizable fluid composition; a 1^(st) step of curing—photocuring, insitu, the circular layer of the first polymerizable fluid composition inthe female mold half by using a visible light to form a disk havingcurved surfaces; a 2^(nd) step of dosing—dispensing an amount of asecond polymerizable fluid composition, which is free of photochromiccompound, over the partially-cured circular layer on the molding surfaceof the female mold half; and a 2nd step of curing—thermally curing thesecond polymerizable fluid composition in the mold cavity formed betweenthe the molding surfaces of the female mold half and a male mold half.

It is found that the curing of the first polymerizable fluid compositioncan be achieved by using visible light irradiation exposed on thecircular layer in the female mold half. After the partial photocuring,unpolymerized polymerizable components and the thermal free-radicalinitiator in the disk will not be able to significantly diffuse into andto blend with the second polymerizable fluid composition. But, thesecond polymerizable fluid composition may still be able to diffuse, atleast partially, into the cured disk in the molding assembly due torelatively longer thermal curing time. Then, the subsequent thermalcuring step will produce contact lenses, each of which comprises acentral photochromic zone that has a diameter of about 13 mm or less andis concentric with the central axis of the unprocessed hydrogel contactlens.

A method of the invention can offer the following advantages. First, amethod of the invention can ensure the physical integrity of producedhydrogel contact lenses. It can also avoid issue of delamination. It isbelieved that due to relatively long curing time required for thermalcuring step, at least some polymerizable components of the secondpolymerizable fluid composition can penetrate deep into the disk andsubsequently be crosslinked in the presence of the thermal initiator inthe disk to form interpenetrating networks with the polymer matrix ofthe disk. It is further believed that during thermal curing step,crosslinked and interpenetrating network can be formed in the boundarybetween the disk and the remaining parts of the hydrogel contact lens.Further, the photochromic functionality is limited in the optical zoneof a contact lens, i.e., over the pupil area of an eye when being worn.Any color associated with the photochromic functionality would haveminimized adverse impacts upon the cosmetic aspect of the hydrogelcontact lens. In addition, use of visible light free-radicalphotoinitiator can minimize the UV-induced degradation of photochromiccompounds.

In some aspects, the invention provides a method for producing hydrogelcontact lenses, comprising the steps of: (1) obtain a firstpolymerizable fluid composition and a second polymerizable fluidcomposition, wherein the first polymerizable fluid composition comprisesat least one visible-light free-radical photoinitiator, at least onethermal free-radical initiator, at least one first polymerizablematerial, and at least one photochromic compound, wherein the secondpolymerizable fluid composition comprises said at least one thermalfree-radical initiator and at least one second polymerizable materialand is free of any photochromic compound, wherein the firstpolymerizable fluid composition has a curing time as determined inphoto-rheology study using a visible light at a specified intensity; (2)obtaining a lens mold, wherein the lens mold comprises a female moldhalf having a first molding surface defining the anterior surface of acontact lens to be molded and a male mold half having a second moldingsurface defining the posterior surface of the contact lens to be molded,wherein the female and male mold halves are configured to receive eachother such that a mold cavity is formed between the first and secondmolding surfaces when the mold is closed; (3) applying an amount of thefirst polymerizable fluid composition onto a central zone of the firstmolding of the female mold half to form a circular layer of the firstpolymerizable fluid composition, wherein the circular layer has adiameter of about 13.00 mm or less; (4) actinically curing the circularlayer of the first polymerizable fluid composition to form a disk havingcurved surface, wherein the step of actinically curing is carried out byirradiating the circular layer of the first polymerizable fluidcomposition with the visible light at the specified intensity for atleast 30% (preferably at least about 50%, more preferably at least about70%, even more preferably at least about 90%) of the curing time; (5)dispensing an amount of the second polymerizable fluid composition overthe disk on the central zone of the first molding surface; (6) closingthe female mold half with the male mold half to form a molding assemblycomprising the disk immersed in the second polymerizable fluidcomposition within the mold cavity; (7) thermally curing the secondpolymerizable fluid composition with the disk immersed therein in themolding assembly to form an unprocessed hydrogel contact lens having acentral photochromic zone that has a diameter of about 13 mm or less, isconcentric with the central axis of the unprocessed hydrogel contactlens; (8) separating the molding assembly into the male and female moldhalves, with the unprocessed hydrogel contact lens adhered onto alens-adhered mold half which is one of the male and female mold halves;(9) removing the unprocessed hydrogel contact lens from the lens-adheredmold half; and (10) subjecting the unprocessed hydrogel contact lens topost-molding processes including a hydration process and one or moreother processes selected from the group consisting of extraction,surface treatment, packaging, sterilization, and combinations thereof.

Any polymerizable materials known or suitable for forming hydrogelcontact lenses can be used in the invention.

In one embodiment, the first and second polymerizable fluid compositionsboth are capable of forming a non-silicone hydrogel and said at leastone first and second polymerizable materials independent of each otherare either (1) a first monomer mixture comprising (a) at least onehydrophilic vinylic monomer and (b) at least one component selected fromthe group consisting of at least one non-silicone vinylic crosslinker, anon-silicone hydrophobic vinylic monomer, a UV-absorbing vinylicmonomer, a polymerizable UV/HEVL-absorbing compound, and combinationsthereof; or (2) a reactive mixture comprising (a) one or morewater-soluble non-silicone prepolymers and optionally (b) at least onecomponent selected from the group consisting of a hydrophilic vinylicmonomer, a non-silicone vinylic crosslinker, a non-silicone hydrophobicvinylic monomer, a UV-absorbing vinylic monomer, a polymerizableUV/HEVL-absorbing compound, and combinations thereof.

In another embodiment, the first and second polymerizable fluidcomposition both are capable of forming a silicone hydrogel and said atleast one first and second polymerizable materials are a second monomermixture comprising (a) at least one silicone-containing vinylic monomer,(b) at least one polysiloxane vinylic crosslinker, at least onenon-silicone vinylic crosslinker, or both, (c) at least one hydrophilicvinylic monomer, (d) at least one free-radical initiator, and optionally(e) at least one component selected from the group consisting of anon-silicone hydrophobic vinylic monomer, a UV-absorbing vinylicmonomer, a polymerizable UV/HEVL-absorbing compound, and combinationsthereof.

Any hydrophilic vinylic monomer can be used in the invention. Examplesof preferred hydrophilic vinylic monomers are hydrophilic(meth)acrylamido monomer (as described later in this application),hydrophilic (meth)acryloxy monomer (as described later in thisapplication), hydrophilic N-vinyl amide monomer (as described later inthis application), methylene-containing pyrrolidone monomers (i.e.,pyrrolidone derivatives each having a methylene group connected to thepyrrolidone ring at 3- or 5-position) (as described later in thisapplication), vinyl ether monomers (as described later in thisapplication), allyl ether monomers (as described later in thisapplication), phosphorylcholine-containing vinylic monomers (asdescribed later in this application), allyl alcohol, N-2-hydroxyethylvinyl carbamate, N-vinyloxycarbonyl-β-alanine (VINAL),N-vinyloxycarbonyl-α-alanine, and combinations thereof.

Any water-soluble non-silicone prepolymers can be used in the invention.Examples of water-soluble non-silicone prepolymers include withoutlimitation: a water-soluble actinically-crosslinkable poly(vinylalcohol) prepolymer described in U.S. Pat. Nos. 5,583,163 and 6,303,687;a water-soluble vinyl group-terminated polyurethane prepolymer describedin U.S. Pat. No. 6,995,192; derivatives of a polyvinyl alcohol,polyethyleneimine or polyvinylamine, which are disclosed in U.S. Pat.No. 5,849,841; a water-soluble crosslinkable polyurea prepolymerdescribed in U.S. Pat. Nos. 6,479,587 and 7,977,430; crosslinkablepolyacrylamide; crosslinkable statistical copolymers of vinyl lactam,MMA and a comonomer, which are disclosed in U.S. Pat. No. 5,712,356;crosslinkable copolymers of vinyl lactam, vinyl acetate and vinylalcohol, which are disclosed in U.S. Pat. No. 5,665,840;polyether-polyester copolymers with crosslinkable side chains which aredisclosed in U.S. Pat. No. 6,492,478; branched polyalkyleneglycol-urethane prepolymers disclosed in U.S. Pat. No. 6,165,408;polyalkylene glycol-tetra(meth)acrylate prepolymers disclosed in U.S.Pat. No. 6,221,303; crosslinkable polyallylamine gluconolactoneprepolymers disclosed in U.S. Pat. No. 6,472,489.

Any non-silicone vinylic crosslinkers can be used in the invention.Examples of preferred non-silicone vinylic crosslinkers are describedlater in this application.

Any non-silicone hydrophobic vinylic monomers can be used in theinvention. Examples of preferred hydrophobic non-silicone vinylicmonomers can be non-silicone hydrophobic acrylic monomers (e.g., alkyl(meth)acrylates as described below, cycloalkyl (meth)acrylates asdescribed below, phenyl methacrylate, (meth)acrylonitrile, etc.),fluorine-containing acrylic monomers (e.g.,perfluorohexylethyl-thio-carbonyl-aminoethyl-methacrylate,perfluoro-substituted-C₂-C₁₂ alkyl (meth)acrylates described below,etc.), vinyl alkanoates (e.g., vinyl acetate, vinyl propionate, vinylbutyrate, vinyl valerate, etc.), vinyloxy-alkanes (e.g., vinyl ethylether, propyl vinyl ether, n-butyl vinyl ether, isoputyl vinyl ether,cyclohexyl vinyl ether, t-butyl vinyl ether, etc.), substituted orunsubstituted styrenes as described below, vinyl toluene, vinylchloride, vinylidene chloride, 1-butene, and mixtures thereof.

Any suitable perfluoro-substituted-C₂-C₁₂ alkyl (meth)acrylates can beused in the invention. Examples of perfluoro-substituted-C₂-C₁₂ alkyl(meth)acrylates include without limitation 2,2,2-trifluoroethyl(meth)acrylate, tetrafluoropropyl (meth)acrylate, hexafluoro-iso-propyl(meth)acrylate, hexafluorobutyl (meth)acrylate, heptafluorobutyl(meth)acrylate, octafluoropentyl (meth)acrylate, heptadecafluorodecyl(meth)acrylate, pentafluorophenyl (meth)acrylate, and combinationsthereof.

In a preferred embodiment, one or more hydrophobic non-silicone acrylicmonomers and/or substituted or unsubstituted styrenes can be used in theinvention as a reactive diluent (i.e., a blending vinylic monomer) forsolubilizing other polymerizable components in a polymerizablecomposition of the invention.

Examples of such non-silicone hydrophobic acrylic monomers andsubstituted or unsubstituted styrenes include methyl methacrylate, ethylmethacrylate, isopropyl methacrylate, sec-butyl methacrylate, tert-butylmethacrylate, cyclohexyl methacrylate, isobornyl acrylate, isobornylmethacrylate, phenyl methacrylate, 4-tert-butylstyrene, 2-methylstyrene,styrene, 4-ethoxystyrene, 2,4-dimethystyrene, 2,5-dimethylstyrene,3,5-dimethylstyrene, and combinations thereof. More preferably, methylmethacrylate, tert-butyl methacrylate, cyclohexyl methacrylate,isobornyl acrylate, isobornyl methacrylate, or a combination thereof isused in the invention. Even more preferably, methyl methacrylate,tert-butyl methacrylate, cyclohexyl methacrylate, or a combinationthereof is used in the invention.

The term “UV/HEVL-absorbing compound” refers to a compound that canabsorb UV light and high-energy-violet-light (i.e., light havingwavelength between 380 nm and 440 nm). Examples of preferredUV/HEVL-absorbing compounds includes polymerizable UV/HEVL-absorbingcompounds, e.g., Cu-porphrin derivatives each having one or moreethyleneically unsaturated groups, UV/HEVL-absorbing vinylic monomer.

The term “UV/HEVL-absorbing vinylic monomer” refers to a vinylic monomerthat can absorb UV light and high-energy-violet-light (i.e., lighthaving wavelength between 380 nm and 440 nm). Examples of UV-absorbingvinylic monomers and UV/HEVL-absorbing vinylic monomers are known to aperson skilled in the art and are disclosed in the patents and patentapplication publications, e.g., U.S. Pat. No. 9,315,669, US 2018-0081197A1, etc.

Any suitable UV-absorbing vinylic monomers and UV/HEVL-absorbing vinylicmonomers can be used in the invention. Examples of preferredUV-absorbing and UV/HEVL-absorbing vinylic monomers include withoutlimitation: 2-(2-hydroxy-5-vinylphenyl)-2H-benzotriazole,2-(2-hydroxy-5-acrylyloxyphenyl)-2H-benzotriazole,2-(2-hydroxy-3-methacrylamido methyl-5-tert octylphenyl) benzotriazole,2-(2′-hydroxy-5′-methacrylamidophenyl)-5-chlorobenzotriazole,2-(2′-hydroxy-5′-methacrylamidophenyl)-5-methoxybenzotriazole,2-(2′-hydroxy-5-methacryloxy-propyl-3′-t-butyl-phenyl)-5-chlorobenzotriazole,2-(2′-hydroxy-5′-methacryloxypropylphenyl) benzotriazole,2-hydroxy-5-methoxy-3-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)benzylmethacrylate (WL-1),2-hydroxy-5-methoxy-3-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)benzylmethacrylate (WL-5),3-(5-fluoro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzylmethacrylate (WL-2),3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzylmethacrylate (WL-3),3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzylmethacrylate (WL-4),2-hydroxy-5-methoxy-3-(5-methyl-2H-benzo[d][1,2,3]triazol-2-yl)benzylmethacrylate (WL-6),2-hydroxy-5-methyl-3-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)benzylmethacrylate (WL-7),4-allyl-2-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-6-methoxy-phenol(WL-8),2-{2′-Hydroxy-3′-tert-5′[3″-(4″-vinylbenzyloxy)propoxy]phenyl}-5-methoxy-2H-benzotriazole,phenol,2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-ethenyl-(UVAM),2-[2′-hydroxy-5′-(2-methacryloxyethyl)phenyl)]-2H-benzotriazole(2-Propenoic acid, 2-methyl-,2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl ester, Norbloc),2-{2′-Hydroxy-3′-tert-butyl-5′-[3′-methacryloyloxypropoxy]phenyl}-2H-benzotriazole,2-{2′-Hydroxy-3′-tert-butyl-5′-[3′-methacryloyloxypropoxy]phenyl}-5-methoxy-2H-benzotriazole(UV13),2-{2′-Hydroxy-3′-tert-butyl-5′-[3′-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole(UV28),2-[2′-Hydroxy-3′-tert-butyl-5′-(3′-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole(UV23), 2-(2′-hydroxy-5-methacrylamidophenyl)-5-methoxybenzotriazole(UV6), 2-(3-allyl-2-hydroxy-5-methylphenyl)-2H-benzotriazole (UV9),2-(2-Hydroxy-3-methallyl-5-methylphenyl)-2H-benzotriazole (UV12),2-3′-t-butyl-2′-hydroxy-5′-(3″-dimethylvinylsilylpropoxy)-2′-hydroxy-phenyl)-5-methoxybenzotriazole(UV15),2-(2′-hydroxy-5′-methacryloylpropyl-3′-tert-butyl-phenyl)-5-methoxy-2H-benzotriazole(UV16),2-(2′-hydroxy-5′-acryloylpropyl-3′-tert-butyl-phenyl)-5-methoxy-2H-benzotriazole(UV16A), 2-Methylacrylic acid3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-propylester (16-100, CAS #96478-15-8),2-(3-(tert-butyl)-4-hydroxy-5-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenoxy)ethylmethacrylate (16-102); Phenol,2-(5-chloro-2H-benzotriazol-2-yl)-6-methoxy-4-(2-propen-1-yl) (CAS#1260141-20-5);2-[2-Hydroxy-5-[3-(methacryloyloxy)propyl]-3-tert-butylphenyl]-5-chloro-2H-benzotriazole;Phenol, 2-(5-ethenyl-2H-benzotriazol-2-yl)-4-methyl-, homopolymer (9Cl)(CAS #83063-87-0). In accordance with the invention, the polymerizablecomposition comprises about 0.1% to about 3.0%, preferably about 0.2% toabout 2.5%, more preferably about 0.3% to about 2.0%, by weight of oneor more UV-absorbing vinylic monomers, related to the amount of allpolymerizable components in the polymerizable composition.

Any silicone-containing vinylic monomer can be used in the invention.Examples of preferred silicone-containing vinylic monomers can besilicone-containing (meth)acrylamido monomers, silicone-containing(meth)acryloxy monomers, silicone-containing vinylcarbonato monomers, orsilicone-containing vinylcarbamato monomers, each of which comprises abis(trialkylsilyloxy)alkylsilyl group, a tris(trialkylsilyloxy)-silylgroup, or a polysiloxane chain having 2 to 30 siloxane units andterminated with an alkyl, hydroxyalkyl or methoxyalkyl group. Suchpreferred silicone-containing vinylic monomers can be obtained from thecommercial suppliers, or alternatively prepared according to knownprocedures, e.g., similar to those described in U.S. Pat. Nos.5,070,215, 6,166,236, 6,867,245, 7,214,809, 8,415,405, 8,475,529,8,614,261, 8,658,748, 9,097,840, 9,103,965, 9,217,813, 9,315,669, and9,475,827, or by reacting a vinylic monomer having a reactive functionalgroup (e.g., an acid chloride, acid anhydride, carboxyl, hydroxyl,amino, epoxy, isocyanate, aziridine, azlactone, or aldehyde group) witha siloxane-containing compound a reactive group selected from the groupconsisting of a hydroxyalkyl, an aminoalkyl, an alkylaminoalkyl, acarboxyalkyl, an isocyanatoalkyl, an epoxyalkyl, and an aziridinylalkyl,in the presence or absence of a coupling agent under coupling reactionconditions well known to a person skilled in the art.

In a preferred embodiment, said at least one silicone-containing vinylicmonomer comprises at least one silicone-containing (meth)acrylamidomonomer having a bis(trialkylsilyloxy)alkylsilyl group, atris(trialkylsilyloxy)silyl group, or a polysiloxane chain having 2 to30 siloxane units and terminated with an alkyl, hydroxyalkyl ormethoxyalkyl group. Examples of such preferred silicone-containing(meth)acrylamido monomers include without limitation those describedlater in this application.

In another preferred embodiment, said at least one silicone-containingvinylic monomer comprises at least one silicone-containing(meth)acryloxy monomer having a bis(trialkylsilyloxy)alkylsilyl group, atris(trialkylsilyloxy)silyl group, or a polysiloxane chain having 2 to30 siloxane units and terminated with an alkyl, hydroxyalkyl ormethoxyalkyl group. Examples of such preferred silicone-containing(meth)acryloxy monomers include without limitation those described laterin this application.

Any polysiloxane vinylic crosslinkers can be used in the invention.Examples of preferred polysiloxane vinylic crosslinkers include withoutlimitation α,ω-(meth)acryloxy-terminated polydimethylsiloxanes;α,ω-(meth)acrylamido-terminated polydimethylsiloxanes; α,ω-vinylcarbonate-terminated polydimethylsiloxanes; α,ω-vinylcarbamate-terminated polydimethylsiloxanes;bis-3-methacryloxy-2-hydroxypropyloxypropyl polydimethylsiloxanes; thereaction products of glycidyl methacrylate with amino-functionalpolydimethylsiloxanes; the reaction products of an azlactone-containingvinylic monomer (any one of those described above) withhydroxyl-functional polydimethylsiloxanes; polysiloxane-containingmacromer selected from the group consisting of Macromer A, Macromer B,Macromer C, and Macromer D described in U.S. Pat. No. 5,760,100;polysiloxane vinylic crosslinkers disclosed in U.S. Pat. Nos. 4,136,250,4,153,641, 4,182,822, 4,189,546, 4,259,467, 4,260,725, 4,261,875,4,343,927, 4,254,248, 4,355,147, 4,276,402, 4,327,203, 4,341,889,4,486,577, 4,543,398, 4,605,712, 4,661,575, 4,684,538, 4,703,097,4,833,218, 4,837,289, 4,954,586, 4,954,587, 5,010,141, 5,034,461,5,070,170, 5,079,319, 5,039,761, 5,346,946, 5,358,995, 5,387,632,5,416,132, 5,449,729, 5,451,617, 5,486,579, 5,962,548, 5,981,675,6,039,913, 6,762,264, 7,423,074, 8,163,206, 8,480,227, 8,529,057,8,835,525, 8,993,651, 9,187,601, 10,081,697, 10,301,451, and 10,465,047.

One class of preferred polysiloxane vinylic crosslinkers aredi-(meth)acryloyloxy-terminated polysiloxane vinylic crosslinkers eachhaving dimethylsiloxane units and hydrophilized siloxane units eachhaving one methyl substituent and one monovalent C₄-C₄₀ organic radicalsubstituent having 2 to 6 hydroxyl groups, more preferably apolysiloxane vinylic crosslinker of formula (H), are described later inthis application and can be prepared according to the proceduresdisclosed in U.S. patent Ser. No. 10/081,697.

Another class of preferred polysiloxane vinylic crosslinkers are vinyliccrosslinkers each of which comprises one sole polydiorganosiloxanesegment and two terminal (meth)acryloyl groups, which can be obtainedfrom commercial suppliers; prepared by reacting glycidyl (meth)acrylate(meth)acryloyl chloride with a di-amino-terminated polydimethylsiloxaneor a di-hydroxyl-terminated polydimethylsiloxane; prepared by reactingisocyantoethyl (meth)acrylate with di-hydroxyl-terminatedpolydimethylsiloxanes prepared by reacting an amino-containing acrylicmonomer with di-carboxyl-terminated polydimethylsiloxane in the presenceof a coupling agent (a carbodiimide); prepared by reacting acarboxyl-containing acrylic monomer with di-amino-terminatedpolydimethylsiloxane in the presence of a coupling agent (acarbodiimide); or prepared by reacting a hydroxyl-containing acrylicmonomer with a di-hydroxy-terminated polydisiloxane in the presence of adiisocyanate or di-epoxy coupling agent.

Other classes of preferred polysiloxane vinylic crosslinkers arechain-extended polysiloxane vinylic crosslinkers each of which has atleast two polydiorganosiloxane segments linked by a linker between eachpair of polydiorganosiloxane segments and two terminal ethylenicallyunsaturated groups, which can be prepared according to the proceduresdescribed in U.S. Pat. Nos. 5,034,461, 5,416,132, 5,449,729, 5,760,100,7,423,074, 8,529,057, 8,835,525, 8,993,651, 9,187,601, 10,301,451, and10,465,047.

Any hydrophilic vinylic monomers can be used in the invention. Examplesof preferred hydrophilic vinylic monomers are hydrophilic(meth)acrylamido monomer (as described later in this application),hydrophilic (meth)acryloxy monomer (as described later in thisapplication), hydrophilic N-vinyl amide monomer (as described later inthis application), methylene-containing pyrrolidone monomers (i.e.,pyrrolidone derivatives each having a methylene group connected to thepyrrolidone ring at 3- or 5-position) (as described later in thisapplication), vinyl ether monomers (as described later in thisapplication), allyl ether monomers (as described later in thisapplication), phosphorylcholine-containing vinylic monomers (asdescribed later in this application), allyl alcohol, N-2-hydroxyethylvinyl carbamate, N-vinyloxycarbonyl-β-alanine (VINAL),N-vinyloxycarbonyl-α-alanine, and combinations thereof.

In another preferred embodiment, said at least one hydrophilic vinylicmonomer comprises at least one hydrophilic (meth)acrylamido monomer,preferably having 3 to 10 carbon atoms. Examples of preferredhydrophilic (meth)acrylamido monomers are described later in thisapplication. It is believed that such hydrophilic (meth)acrylamidomonomers can be used in increasing the glass transition temperature of aresultant silicone hydrogel material. It is also understood that anyhydrophilic (meth)acrylamido monomers other than those specificallydescribed later in this application can also be used in this invention.

In another preferred embodiment, said at least one hydrophilic vinylicmonomer comprises at least one hydrophilic N-vinyl amide monomer.Examples of preferred hydrophilic N-vinyl amide monomers are describedlater in this application. It is understood that any hydrophilic N-vinylamide monomers other than those specifically described later in thisapplication can also be used in this invention.

In another preferred embodiment, said at least one hydrophilic vinylicmonomer comprises at least one hydrophilic (meth)acryloxy monomer,preferably having 3 to 10 carbon atoms. Examples of preferredhydrophilic (meth)acryloxy monomers are described later in thisapplication. It is understood that any hydrophilic (meth)acryloxymonomers other than those specifically described later in thisapplication can also be used in this invention.

In accordance with the invention, visible lights are used to partiallycure (crosslink) the circular layer of the first polymerizable fluidcomposition. It is believed that the irradiation of visible lights wouldcause minimized degradation to a photochromic compound.

Any suitable visible light free-radical photoinitiators can be used inthe invention Examples of preferred visible light free-radicalphotoinitiators include without limitation acylgermaniumphotoinitiators, benzoylphosphine oxide, acylphosphinate salts, and thelikes.

Examples of benzoylphosphine initiators include2,4,6-trimethylbenzoyldiphenyl-phosphine oxide;bis-(2,6-dichlorobenzoyl)-4-N-propylphenylphosphine oxide; andbis-(2,6-dichlorobenzoyl)-4-N-butylphenylphosphine oxide. One example ofwater-soluble acylphosphinate salts is Lithium phenyl(2,4,6-trimethylbenzoyl) phosphinate, available from Tokyo ChemicalIndustry Co., Ltd.

Any acylgermanium photoinitiators can be used in this invention, so longas they are capable of initiating a free-radical polymerization underirradiation with a light source including a light in the region of about420 to about 500 nm. Examples of acylgermanium photoinitiators areacylgermanium compounds described in U.S. Pat. No. 7,605,190.Preferably, said at least one first and/or second free-radical initiatorcomprises at least one of the following acylgermanium compounds.

Any thermal free-radical initiators can be used in the invention.Suitable thermal free-radical initiators are known to the skilledartisan and comprise, for example peroxides, hydroperoxides,azo-bis(alkyl- or cycloalkylnitriles), persulfates, percarbonates, ormixtures thereof. Examples of preferred thermal free-radical initiatorsinclude without limitation benzoyl peroxide, t-butyl peroxide, t-amylperoxybenzoate, 2,2-bis(tert-butylperoxy)butane,1,1-bis(tert-butylperoxy)cyclohexane,2,5-Bis(tert-butylperoxy)-2,5-dimethylhexane,2,5-bis(tert-butylperoxy)-2,5-dimethyl-3-hexyne,bis(1-(tert-butylperoxy)-1-methylethyl)benzene,1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane,di-t-butyl-diperoxyphthalate, t-butyl hydro-peroxide, t-butylperacetate, t-butyl peroxybenzoate, t-butylperoxy isopropyl carbonate,acetyl peroxide, lauroyl peroxide, decanoyl peroxide, dicetylperoxydicarbonate, di(4-t-butylcyclohexyl)peroxy dicarbonate (Perkadox16S), di(2-ethylhexyl)peroxy dicarbonate, t-butylperoxy pivalate(Lupersol 11); t-butylperoxy-2-ethylhexanoate (Trigonox 21-C50),2,4-pentanedione peroxide, dicumyl peroxide, peracetic acid, potassiumpersulfate, sodium persulfate, ammonium persulfate,2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) (VAZO 33),2,2′-Azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride (VAZO 44),2,2′-azobis(2-amidinopropane) dihydrochloride (VAZO 50),2,2′-azobis(2,4-dimethylvaleronitrile) (VAZO 52),2,2′-azobis(isobutyronitrile) (VAZO 64 or AIBN),2,2′-azobis-2-methylbutyronitrile (VAZO 67),1,1-azobis(1-cyclohexanecarbonitrile) (VAZO 88);2,2′-azobis(2-cyclopropylpropionitrile), 2,2′-azobis(methylisobutyrate),4,4′-Azobis(4-cyanovaleric acid), and combinations thereof. Preferably,the thermal free-radical initiator is 2,2′-azobis(isobutyronitrile)(AIBN or VAZO 64).

A first and second polymerizable fluid compositions of the invention canalso comprise other necessary components known to a person skilled inthe art, such as, for example, visibility tinting agent (e.g., one ormore polymerizable dyes, pigments, or mixtures thereof), antimicrobialagents (e.g., silver nanoparticles), a bioactive agent (e.g., a drug, anamino acid, a polypeptide, a protein, a nucleic acid,2-pyrrolidone-5-carboxylic acid (PCA), an alpha hydroxyl acid, linoleicand gamma linoleic acids, vitamins, or any combination thereof),leachable lubricants (e.g., a non-crosslinkable hydrophilic polymerhaving an average molecular weight from 5,000 to 500,000, preferablyfrom 10,000 to 300,000, more preferably from 20,000 to 100,000 Daltons),leachable tear-stabilizing agents (e.g., a phospholipid, amonoglyceride, a diglyceride, a triglyceride, a glycolipid, aglyceroglycolipid, a sphingolipid, a sphingo-glycolipid, a fatty acidhaving 8 to 36 carbon atoms, a fatty alcohol having 8 to 36 carbonatoms, or a mixture thereof), mold releasing agent, and mixturesthereof, as known to a person skilled in the art.

In accordance with the invention, the first and second polymerizablefluid compositions of the invention can be a solution, a solventlessblend (i.e., a fluid composition free of any non-reactivediluent—organic solvent). It can be prepared according to any techniquesknown to a person skilled in the art.

A first or second polymerizable fluid composition of the invention canalso be any known hydrogel lens formulations.

Numerous non-silicone hydrogel lens formulations have been described innumerous patents and patent applications published by the filing date ofthis application and have been used in producing commercial non-siliconehydrogel contact lenses. Examples of commercial non-silicone hydrogelcontact lenses include, without limitation, alfafilcon A, acofilcon A,deltafilcon A, etafilcon A, focofilcon A, helfilcon A, helfilcon B,hilafilcon B, hioxifilcon A, hioxifilcon B, hioxifilcon D, methafilconA, methafilcon B, nelfilcon A, nesofilcon A, ocufilcon A, ocufilcon B,ocufilcon C, ocufilcon D, omafilcon A, phemfilcon A, polymacon,samfilcon A, telfilcon A, tetrafilcon A, vifilcon A, etc.

Numerous SiHy lens formulations have been described in numerous patentsand patent applications published by the filing date of this applicationand have been used in producing commercial SiHy contact lenses. Examplesof commercial SiHy contact lenses include, without limitation,asmofilcon A, balafilcon A, comfilcon A, delefilcon A, efrofilcon A,enfilcon A, fanfilcon A, galyfilcon A, lotrafilcon A, lotrafilcon B,narafilcon A, narafilcon B, senofilcon A, senofilcon B, senofilcon C,smafilcon A, somofilcon A, stenfilcon A, etc.

Where a first or second polymerizable fluid composition of the inventionis a solution. It can be prepared by dissolving all of the desirablecomponents in any suitable solvent known to a person skilled in the art.Example of suitable solvents includes without limitation, water,tetrahydrofuran, tripropylene glycol methyl ether, dipropylene glycolmethyl ether, ethylene glycol n-butyl ether, ketones (e.g., acetone,methyl ethyl ketone, etc.), diethylene glycol n-butyl ether, diethyleneglycol methyl ether, ethylene glycol phenyl ether, propylene glycolmethyl ether, propylene glycol methyl ether acetate, dipropylene glycolmethyl ether acetate, propylene glycol n-propyl ether, dipropyleneglycol n-propyl ether, tripropylene glycol n-butyl ether, propyleneglycol n-butyl ether, dipropylene glycol n-butyl ether, tripropyleneglycol n-butyl ether, propylene glycol phenyl ether dipropylene glycoldimethyl ether, polyethylene glycols, polypropylene glycols, ethylacetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate,i-propyl lactate, methylene chloride, 2-butanol, 1-propanol, 2-propanol,menthol, cyclohexanol, cyclopentanol and exonorborneol, 2-pentanol,3-pentanol, 2-hexanol, 3-hexanol, 3-methyl-2-butanol, 2-heptanol,2-octanol, 2-nonanol, 2-decanol, 3-octanol, norborneol, tert-butanol,tert-amyl, alcohol, 2-methyl-2-pentanol, 2,3-dimethyl-2-butanol,3-methyl-3-pentanol, 1-methylcyclohexanol, 2-methyl-2-hexanol,3,7-dimethyl-3-octanol, 1-chloro-2-methyl-2-propanol,2-methyl-2-heptanol, 2-methyl-2-octanol, 2-2-methyl-2-nonanol,2-methyl-2-decanol, 3-methyl-3-hexanol, 3-methyl-3-heptanol,4-methyl-4-heptanol, 3-methyl-3-octanol, 4-methyl-4-octanol,3-methyl-3-nonanol, 4-methyl-4-nonanol, 3-methyl-3-octanol,3-ethyl-3-hexanol, 3-methyl-3-heptanol, 4-ethyl-4-heptanol,4-propyl-4-heptanol, 4-isopropyl-4-heptanol, 2,4-dimethyl-2-pentanol,1-methylcyclopentanol, 1-ethylcyclopentanol, 1-ethylcyclopentanol,3-hydroxy-3-methyl-1-butene, 4-hydroxy-4-methyl-1-cyclopentanol,2-phenyl-2-propanol, 2-methoxy-2-methyl-2-propanol2,3,4-trimethyl-3-pentanol, 3,7-dimethyl-3-octanol, 2-phenyl-2-butanol,2-methyl-1-phenyl-2-propanol and 3-ethyl-3-pentanol,1-ethoxy-2-propanol, 1-methyl-2-propanol, t-amyl alcohol, isopropanol,1-methyl-2-pyrrolidone, N,N-dimethylpropionamide, dimethyl formamide,dimethyl acetamide, dimethyl propionamide, N-methyl pyrrolidinone, andmixtures thereof. Preferably, a polymerizable composition is a solutionof all the desirable components in water, 1,2-propylene glycol, apolyethyleneglycol having a molecular weight of about 400 Daltons orless, or a mixture thereof.

Where a first or second polymerizable fluid composition of the inventionis a solventless blend, it can be prepared by mixing all polymerizablecomponents and other necessary component. A solventless polymerizablecomposition typically comprises at least one blending vinylic monomer asa reactive solvent for dissolving all other polymerizable components ofthe solventless polymerizable composition. Examples of preferredblending vinylic monomers are described above and later in thisapplication. Preferably, methyl methacrylate is used as a blendingvinylic monomer in preparing a solventless polymerizable composition.

Any polymerizable photochromic compounds can be used in this invention.Examples of preferred polymerizable photochromic compounds includepolymerizable naphthopyrans, polymerizable benzopyrans, polymerizableindenonaphthopyrans, polymerizable phenanthropyrans, polymerizablespiro(benzindoline)-naphthopyrans, polymerizablespiro(indoline)benzopyrans, polymerizable spiro(indoline)-naphthopyrans,polymerizable spiro(indoline)quinopyrans, polymerizablespiro(indoline)-pyrans, polymerizable naphthoxazines, polymerizablespirobenzopyrans; polymerizable spirobenzopyrans, polymerizablespirobenzothiopyrans, polymerizable naphthacenediones, polymerizablespirooxazines, polymerizable spiro(indoline)naphthoxazines,polymerizable spiro(indoline)pyridobenzoxazines, polymerizablespiro(benzindoline)pyridobenzoxazines, polymerizablespiro(benzindoline)naphthoxazines, polymerizablespiro(indoline)-benzoxazines, polymerizable diarylethenes, andcombinations thereof, as disclosed in U.S. Pat. Nos. 4,929,693,5,166,345, 6,017,121, 7,556,750, 7,584,630, 7,999,989, 8,158,037,8,697,770, 8,741,188, 9,052,438, 9,097,916, 9,465,234, 9,904,074,10,197,707, 6,019,914, 6,113,814, 6,149,841, 6,296,785, and 6,348,604.

Various photochromic compounds are disclosed in the patents andpublished patent applications and can be obtained from commercialsources or prepared by following the procedures described in the patentsand literatures. Examples of preferred photochromic compounds includewithout limitation naphthopyrans, indeno-fused naphthopyrans (i.e.,indeno-naphthopyrans), heterocyclic ring-fused naphthopyrians,benzopyrans, phenanthropyrans, quinopyrans, quinolinopyrans,fluoroanthenopyrans, anthracene-fused pyrans, tetracene-fused pyrans,spiro(benzindoline)naphthopyrans, spiro(indoline)naphthopyrans,spiro(indoline)-benzopyrans, spiro(indoline)quinopyrans,spiro(indoline)pyrans, naphthoxazines, spirobenzopyrans,spirobenzothiopyrans, naphthacenediones, benzoxazines, spirooxazines,naphthoxazines, spiro(benzindoline)naphthoxazines,spiro(indoline)naphthoxazines, spiro(indoline)pyrido-benzoxazines,spiro(indoline) benzoxazines, spiro(benzindoline)-benzoxazines,spiro(benzindoline)pyridobenzoxazines,spiro(indoline)fluoranthenoxazines, spiro(indoline)-quinoxazines,spiropiperidine-naphthopyrans, piro(indoline)pyronobenzo-xazinones,benzospiropyrans, naphthospiropyrans, spirobenzoxazine-pyrrolopyridines,spironaphthoxazine-pyrrolopyrridines, spiro-oxazepin-benzoxazines,spiro-oxazepin-naphthoxazines, spiro(indoline)benzothiazoloxazines,spiro(indoline)benzopyrroloxazines, spiro(indoline)quinazolino-oxazines,spiro(indoline)-anthracenobenzoxazines, benzofuro-benzopyrans,benzothienobenzopyrans, naphthofurobenzopyrans,benzopyrano-fusednaphthopyrans, spiro(isoindoline)-naphthoxazines,spiro(isoindoline)benzoxazines, etc.

Such photochromic compounds are disclosed in U.S. Pat. Nos. 3,100,778,3,562,172, 3,567,605, 3,578,602, 3,671,543, 4,215,010, 4,342,668,4,440,672, 4,634,767, 4,636,561, 4,637,698, 4,699,473, 4,719,296,4,720,547, 4,772,700, 4,784,474, 4,785,097, 4,816,584, 4,818,096,4,826,977, 4,831,142, 4,880,667, 4,929,693, 4,931,219, 4,931,221,4,959,471, 4,980,089, 4,986,934, 5,055,576, 5,066,818, 5,110,922,5,114,621, 5,139,707, 5,166,345, 5,171,636, 5,180,524, 5,186,867,5,200,116, 5,238,931, 5,238,981, 5,244,602, 5,274,132; 5,340,857,5,369,158, 5,384,077, 5,395,567, 5,399,687, 5,405,958, 5,411,679,5,429,774, 5,451,344, 5,458,814; 5,458,815, 5,464,567, 5,466,398,5,514,817; 5,520,853, 5,552,090, 5,552,091, 5,565,147, 5,573,712;5,578,252, 5,585,042, 5,623,005, 5,637,262, 5,637,709, 5,645,767;5,650,098, 5,651,923, 5,656,206; 5,658,500, 5,658,501, 5,674,432,5,698,141, 5,723,072, 5,728,758, 5,730,908, 5,744,070, 5,759,450,5,783,116, 5,801,243, 5,808,063, 5,811,034, 5,831,090, 5,833,885,5,869,658; 5,879,592, 5,891,368, 5,955,520; 5,961,892; 5,981,634,5,998,520, 6,004,486, 6,017,121, 6,018,059; 6,019,914, 6,022,495,6,022,497; 6,030,555, 6,034,193, 6,065,836, 6,106,744, 6,106,744,6,107,395, 6,113,814, 6,146,554; 6,149,841, 6,153,126, 6,221,284,6,248,264; 6,296,785, 6,315,928; 6,342,459; 6,348,604, 6,353,102,6,414,057, 6,478,988, 6,630,597, 7,556,750, 7,584,630, 7,999,989,8,158,037, 8,697,770, 8,698,117, 8,741,188, 9,029,532, 9,028,728,9,052,438, 9,097,916, 9,465,234, 9,487,499, 9,904,074, 10,197,707,10,501,446, 10,532,997, and 10,502,998 and are also described in thetexts, Techniques in Chemistry, Volume Ill. “Photochromism”, Chapter 3(Glenn H. Brown, Editor, John Wiley and Sons, Inc., New York, 1971) andin “Chromic Phenomena: Technological Applications of Colour Chemistry”(P. Bamfield, RSC Books (2001)). Derivatives of these compounds thatinclude various Substituents can be Synthesized from this teaching bypeople skilled in the art.

A polymerizable photochromic compound can be obtained by reacting areactive (meth)acrylamido or (meth)acryloxy monomer having a firstreactive functional group (—COCl, —COBr, —COOH, —NHR_(N2), —NCO, —OH,—CHO,

in which R₀ is hydrogen or methyl and R_(N2) is hydrogen, a linear orbranched C₁-C₁₅ alkyl, cyclohexyl, cyclopentyl, a substituted orunsubstituted phenyl, or a substituted- or unsubstituted-phenyl-C₁-C₆alkyl) with a reactive photochromic compound having a second reactivefunctional group (—COOH, —NHR_(N2),

—NCO, —OH, —SH, —CHO,

in the absence or presence of a coupling agent (i.e., having two of thereactive functional groups listed above) under well known couplingreaction conditions, to form a photochromic compound.

Non-limiting examples of coupling reactions under various reactionconditions between a pair of matching co-reactive functional groupsselected from the group preferably consisting of primary group,secondary amino group, hydroxyl group, carboxyl group, acid anhydridegroup, aldehyde group, isocyanate group, epoxy group, aziridine group,azlactone group and thiol group, are given below for illustrativepurposes. A primary/secondary amino group reacts with aldehyde or ketonegroup to form a Schiff base which may further be reduced into an aminebond; a primary/secondary amino group —NHR (in which R is hydrogen orC₁-C₆ alkyl) reacts with an acid chloride or bromide group or with anacid anhydride group to form an amide linkage (—CO—NR—); an amino group—NHR reacts with a N-hydroxysuccinimide ester group to form an amidelinkage; an amino group —NHR reacts with a carboxylic acid group in thepresence of a coupling agent—carbodiimide (e.g.,1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC),N,N′-dicyclohexylcarbodiimide (DCC),1-cylcohexyl-3-(2-morpholinoethyl)carbodiimide, diisopropylcarbodiimide, or mixtures thereof) and N-hydroxysuccinimide to form anamide linkage; an amino group —NHR reacts (ring-opening) with anazlactone group to form an alkylene-diamido linkage(—CONH—CR¹R²—(CH₂)_(p1)—CONH—); an amino group —NHR reacts with anisocyanate group to form a urea linkage (—NR—C(O)—NH— with R as definedabove); an amino group —NHR reacts with an epoxy or aziridine group toform an amine bond (—C—NR—); a hydroxyl reacts with an isocyanate toform a urethane linkage; a hydroxyl reacts with an epoxy or aziridine toform an ether linkage (—O—); a hydroxyl reacts with an acid chloride orbromide group or with an acid anhydride group to form an ester linkage;a carboxyl group reacts with an epoxy group to form an ester bond; athiol group (—SH) reacts with an isocyanate to form a thiocarbamatelinkage (—N—C(O)—S—); a thiol group reacts with an epoxy or aziridine toform a thioether linkage (—S—); a thiol group reacts with an acidchloride or bromide group or with an acid anhydride group to form athioester linkage; a thiol group reacts with an azlactone group in thepresence of a catalyst to form a linkage (—CONH—CR¹R²—(CH₂)_(p1)—CO—S—);a thiol group reacts with an ene group or vinylsulfonyl group based onthiol-ene “click” reaction under thiol-ene reaction conditions to form athioether linakge (—S—); a thiol group reacts with a (meth)acryloylgroup based on Michael Addition under appropriate reaction conditions toform a thioether linkage.

The reactions conditions for the above described coupling reactions aretaught in textbooks and are well known to a person skilled in the art.

Any coupling agents, each of which has two reactive functional groups,may be used in the coupling reactions. A coupling agent having tworeactive functional groups can be: a diisocyanate compound; a di-acidhalide compound; a di-carboxylic acid compound; a di-carboxylic acidanhydride compound; a diamine compound; a diol compound; a di-epoxycompound; a di-aziridine compound; di-azlactone compound; a di-enecompound; a divinylsulfone compound; a di-thiol compound; a thiolactonecompound; an amino acid compound; a hydroxy-containing amine compound;an amine compound having one hydroxyl or ketone group; ahydroxy-containing carboxylic acid compound; a mercaptane having ahydroxyl, carboxyl or amino group.

For example, a diisocyanate, di-carboxylic acid (preferably adi-carboxylic acid anhydride), di-aziridine, di-epoxy, or di-azlactonecompound can be used in the coupling of the first and second reactivefunctional groups when they are different or same and are selected fromthe group consisting of hydroxyl, primary amino, secondary amino, andthiol groups; a di-amine, di-hydroxyl, di-thiol, hydroxy-containingamine, or hydroxy-containing thiol compound can be used in the couplingof the first and second reactive functional groups when they aredifferent or same and are selected from the group consisting ofisocyanate, epoxy, aziridine, and carboxylic acid groups; a di-epoxycompound can be used in the coupling of the first and second reactivefunctional groups when they both are carboxylic acid groups; a di-aminecompound can be used in the coupling of the first and second reactivefunctional groups when they both are aldehyde groups. A person skilledin the art knows well how to select one or more coupling agents, basedon selectivity and/or differential reactivity of a given reactivefunctional group, to link the first and second reactive functionalgroups to form a photochromic polydiorganosiloxane vinylic crosslinkerof the invention.

Examples of commercially available di-carboxylic acid anhydrides includewithout limitation succinic acid anhydride, methylsuccinic anhydride,2,2-dimethylsuccinic anhydride, 2,3-dimethylsuccinic acid, glutaric acidanhydride, 3,3-dimethylglutaric anhydride, 2,2-dimethylglutaricanhydride, 3-methylglutaric anhydride, 3,3-tetramethylglutaricanhydride, diglycolic anhydride, adipic anhydride, etc.

Any suitable C₃-C₂₄ di-carboxylic acid compounds can be used in theinvention. Examples of preferred di-carboxylic acid compounds includewithout limitation a linear or branched C₃-C₂₄ aliphatic dicarboxylicacid, a C₅-C₂₄ cycloaliphatic or aliphatic-cycloaliphatic dicarboxylicacid, a C₆-C₂₄ aromatic or araliphatic dicarboxylic acid, a dicarboxylicacid which contains amino or imido groups or N-heterocyclic rings, andcombinations thereof. Examples of suitable aliphatic dicarboxylic acidsare: oxalic acid, malonic acid, succinic acid, glutaric acid, adipicacid, pimelic acid, suberic acid, azelaic acid, sebacic acid,undecanedioic acid, dodecanedioic acid, dimethylmalonic acid,octadecylsuccinic acid, trimethyladipic acid, and dimeric acids(dimerisation products of unsaturated aliphatic carboxylic acids, suchas oleic acid). Examples of suitable cycloaliphatic dicarboxylic acidsare: 1,3-cyclobutanedicarboxylic acid, 1,3-cyclopentanedicarboxylicacid, 1,3- and 1,4-cyclohexanedicarboxylic acid, 1,3- and1,4-dicarboxylmethylcyclohexane, 4,4′-dicyclohexyldicarboxylic acid.Examples of suitable aromatic dicarboxylic acids are: terephthalic acid,isophthalic acid, o-phthalic acid, 1,3-, 1,4-, 2,6- or2,7-naphthalenedicarboxylic acids, 4,4′-biphenyldicarboxylic acid,2,2′-biphenyl-dicarboxylic acid, 4,4′-diphenylsulphone-dicarboxylicacid, 1,1,3-trimethyl-5-carboxyl-3-(p-carboxyphenyl)-indane,4,4′-diphenyl ether-dicarboxylic acid, bis-p-(carboxylphenyl)-methane.

Any suitable diacid halides can be used in the invention. Examples ofpreferred diacid halide include without limitations fumaryl chloride,suberoyl chloride, succinyl chloride, phthaloyl chloride, isophthaloylchloride, terephthaloyl chloride, sebacoyl chloride, adipoyl chloride,trimethyladipoyl chloride, azelaoyl chloride, dodecanedioic acidchloride, succinic chloride, glutaric chloride, oxalyl chloride, dimeracid chloride, and combinations thereof.

Any suitable diamines can be used in the invention. An organic diaminecan be a linear or branched C₂-C₂₄ aliphatic diamine, a C₅-C₂₄cycloaliphatic or aliphatic-cycloaliphatic diamine, or a C₆-C₂₄ aromaticor alkyl-aromatic diamine. A preferred organic diamine isN,N′-bis(hydroxyethyl)ethylenediamine, N,N′-dimethylethylenediamine,ethylenediamine, N,N′-dimethyl-1,3-propanediamine,N,N′-diethyl-1,3-propanediamine, N-methyl-1,3-diaminopropane,N-methylethylenediamine, N-ethylethylenediamine,N-isopropyl-1,3-propanediamine, N-propyl-1,3-propanediamine,N-butylethylenediamine, 2,2-dimethyl-1,3-propanediamine,1,4-butanediamine, 1,5-pentanediamine, hexamethylenediamine,2-Methyl-1,5-pentanediamine, 1,6-hexamethylenediamine,N,N′-dimethyl-1,6-hexamethylenediamine,2,2,4(2,4,4)-trimethyl-1,6-hexanediamine, 1,3-diamino-2-propanol,1,2-diaminoethane-1,2-diol, 1,1-diaminoethane-1,2-diol,1,4-diamino-2,3-butanediol, 1,3-cyclopentanediamine,1,4-diaminocyclohexane, 1,3-Bis(aminomethyl)cyclohexane,4,4′-diaminodicyclohexylmethane,4,4′-methylenebis(2-methylcyclohexylamine), isophorone diamine(3-aminomethyl-3,5,5-trimethylcyclohexylamine), m-xylylene diamine,p-xylylene diamine, piperazine, 1-(2-aminoethyl)piperazine,1,4-bis(3-aminopropyl)piperazine, 2-piperazinoethylamine,1-Boc-piperazine, 4-(2-aminoethyl)-1-Boc-piperazine,1-(2-N-Boc-aminoethyl)piperazine, 4-(2-aminoethyl)-1-Boc-piperazine,4-aminopiperidine, 3-aminopiperidine, 4-aminomethylpiperidine,2-aminomethylpiperidine, 1-Boc-piperidine-4-carboxaldehyde,1-Boc-piperidine-4-acetaldehyde, etc.

Any suitable C₄-C₂₄ diisocyanates can be used in the invention. Examplesof preferred diisocyanates include without limitation tetramethylenediisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate,heptamethylene diisocyanate, 1,6-diisocyanato-2,2,4-trimethylhexane,octamethylene diisocyanate, dodecamethylene diisocyanate, cyclohexanediisocyanate, 1,3-bis-(4,4′-isocyantomethyl)cyclohexane, isophoronediisocyanate, 4,4′-dicyclohexylmethane diisocyanate, toluenediisocyanate, 4,4′-diphenyl diisocyanate, 4,4′-diphenylmethanediisocyanate, p-phenylene diisocyanate, etc.

Any suitable di-epoxy compounds can be used in the invention. Examplesof preferred di-epoxy compounds are neopentyl glycol diglycidyl ether,1,3-butadiene diepoxide, 1,4-butanediol diglycidyl ether,1,2,7,8-diepoxyoctane, 3,4-epoxycyclohexylmethyl-3,4-epoxy-cyclohexane,3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate,vinylcyclohexene dioxide, 1,6-hexanediol diglycidyl ether, glyceroldiglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycoldiglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycoldiglycidyl ether, dipropylene glycol diglycidyl ether, polypropyleneglycol diglycidyl ether, bis[4-(glycidyloxy)phenyl]methane, Bisphenol Adiglycidyl ether (2,2-Bis[4-(glycidyloxy)phenyl]-propane), Bisphenol Apropoxylate diglycidyl ether, and combinations thereof.

Any suitable C₂-C₂₄ diols (i.e., compounds with two hydroxyl groups) canbe used in the invention. Examples of preferred diols include withoutlimitation ethylene glycol, diethylene glycol, triethylene glycol,tetraethylene glycol, polyethylene glycol, propylene glycol,1,4-butanediol, various pentanediols, various hexanediols, variouscyclohexanediols, 1,4-bis(2-hydroxyethyl)piperazine, bisphenol A,bisphenol F, 4,4′-methylenediphenol, and combination thereof.

Any amino acids can be used in the invention. Examples of amino acidsinclude without limitation glycine, proline, alanine, valine,isoleucine, leucine, 2-aminoisobutyric acid, 4-aminobutyric acid,3-aminoisobutyyric acid, 3-amino-butyric acid, β-alanine,1-amino-3-cyclopentane carboxylic acid, 3-aminocyclohexanecarboxylicacid, pyrrolidine-3-carboxylic acid, 4-piperidinecarboxylic acid,3-piperidinecarboxylic acid, 1-piperazineacetic acid, etc.

Examples of compounds having one amino group and one hydroxyl oraldehyde group (or ketone group) include without limitation1-piperazinepropanol, 2-[2-(1-piperazinyl)ethoxy]-ethanol,4-amino-1-piperazineethanol, 4-piperidinemethanol,1-Boc-piperidine-4-carboxaldehyde, 4-formylpiperidine,N-Boc-4-piperidineacetaldehyde, etc.

Preferred reactive (meth)acrylamido or (meth)acryloxy monomers withoutlimitation include those described later in this application.

Preferred photochromic compounds without limitation include withoutlimitation those compounds that are described later in this applicationand can be obtained from commercial suppliers or prepared according toprocedures described in the patents discussed above and in the textsdescribed above.

Lens molds for making contact lenses including hydrogel contact lensesare well known to a person skilled in the art and, for example, areemployed in cast molding or spin casting. For example, a mold (for castmolding) generally comprises at least two mold sections (or portions) ormold halves, i.e. first and second mold halves. The first mold halfdefines a first molding (or optical) surface and the second mold halfdefines a second molding (or optical) surface. The first and second moldhalves are configured to receive each other such that a lens-formingcavity is formed between the first molding surface and the secondmolding surface. The molding surface of a mold half is thecavity-forming surface of the mold and in direct contact with thepolymerizable composition.

Methods of manufacturing mold sections for cast molding a contact lensare generally well known to those of ordinary skill in the art. Theprocess of the present invention is not limited to any particular methodof forming a mold. In fact, any method of forming a mold can be used inthe present invention.

In general, a mold comprises at least two mold halves (or moldsections), one male half and one female mold half. The male mold halfhas a first molding (or optical) surface which is in direct contact witha polymerizable composition for cast molding of a contact lens anddefines the posterior (concave) surface of a molded contact lens; andthe female mold half has a second molding (or optical) surface which isin direct contact with the polymerizable composition and defines theanterior (convex) surface of the molded contact lens. The male andfemale mold halves are configured to receive each other such that alens-forming cavity is formed between the first molding surface and thesecond molding surface.

The mold halves can be formed through various techniques, such asinjection molding. Methods of manufacturing mold halves for cast-moldinga contact lens are generally well known to those of ordinary skill inthe art. The process of the present invention is not limited to anyparticular method of forming a mold. In fact, any method of forming amold can be used in the present invention. The first and second moldhalves can be formed through various techniques, such as injectionmolding or lathing. Examples of suitable processes for forming the moldhalves are disclosed in U.S. Pat. Nos. 4,444,711; 4,460,534; 5,843,346;and 5,894,002.

Virtually all materials known in the art for making molds can be used tomake molds for making contact lenses. For example, polymeric materials,such as polyethylene, polypropylene, polystyrene, PMMA, Topas® COC grade8007-S10 (clear amorphous copolymer of ethylene and norbornene, fromTicona GmbH of Frankfurt, Germany and Summit, N.J.), or the like can beused. Other materials that allow UV light transmission could be used,such as quartz glass and sapphire.

In accordance with the invention, the first or second polymerizablefluid composition can be dispensed onto the molding surface of a femalemold half according to any known techniques.

In accordance with the invention, any visible light can be used in thepartial curing step. Preferably, a visible light in a region between 420nm to 500 nm is used in the invention. Light source can be any onesemitting light in the 420-500 nm range sufficient to activateacylgermanium photoinitiators. Blue-light sources are commerciallyavailable and include: the Palatray CU blue-light unit (available fromHeraeus Kulzer, Inc., Irvine, Calif.), the Fusion F450 blue light system(available from TEAMCO, Richardson, Tex.), Dymax Blue Wave 200, LEDlight sources from Opsytec (435 nm, 445 nm, 460 nm), and the GE 24″ bluefluorescent lamp (available from General Electric Company, U.S.). Apreferred blue-light source is the LED from Opsytec (those describedabove).

A specific amount of a second polymerizable fluid composition istypically dispensed into a female mold half over thepartially-crosslinked (partially-cured) circular layer by means of adispensing device and then a male mold half is put on and the mold isclosed. As the mold closes, any excess second polymerizable fluidcomposition is pressed into an overflow provided on the female mold half(or alternatively on the male mold half).

The molding assembly (i.e., the closed mold containing the secondpolymerizable fluid composition and the partially-crosslinked circularlayer immersed therein) is subsequently cured thermally, as known to aperson skilled in the art, to produce a molded unprocessed hydrogelcontact lens.

The thermal curing (i.e., polymerization) of the second polymerizablefluid composition and the partially-crosslinked circular layer immersedtherein in the molding assembly can be carried out conveniently in anoven at a temperature of from 25 to 120° C. and preferably 40 to 100°C., as well known to a person skilled in the art. The reaction time mayvary within wide limits, but is conveniently, for example, from 1 to 24hours or preferably from 2 to 12 hours. It is advantageous to previouslydegas the silicone-hydrogel-lens-forming composition and to carry outsaid copolymerization reaction under an inert atmosphere, e.g., under N₂or Ar atmosphere.

After curing, the molds can be opened according to any techniques knownto a person skilled in the art. After the mold is separated, the moldedunprocessed hydrogel contact lens adheres to one of the male and femalemold halves.

The unprocessed hydrogel contact lens adhered on the lens-adhered moldhalf can be removed from the lens-adhered mold half and then subject toone or more post molding processes.

For example, unprocessed hydrogel contact lens can be extracted with aliquid extraction liquid medium to remove unpolymerized polymerizablecomponents and formed and oligomers. In accordance with the invention,the extraction liquid medium is any solvent capable of dissolving theorganic solvent, unpolymerized polymerizable materials, and oligomers inthe dry contact lens. Water, any organic solvents known to a personskilled in the art, or a mixture thereof can be used in the invention.Preferably, the organic solvents used extraction liquid medium arewater, a buffered saline, a C₁-C₃ alkyl alcohol, 1,2-propylene glycol, apolyethyleneglycol having a number average molecular weight of about 400Daltons or less, a C₁-C₆ alkylalcohol, or combinations thereof.

The hydrogel contact lenses can also be subjected to further processes,such as, for example, surface treatment (for example, such as, plasmatreatment, chemical treatments, the grafting of hydrophilic monomers ormacromers onto the surface of a lens, Layer-by-layer coating, in-packagecrosslinking of a thermally-reactive hydrophilic polymeric material,etc.); packaging in lens packages with a packaging solution which cancontain about 0.005% to about 5% by weight of a wetting agent (e.g., ahydrophilic polymer), a viscosity-enhancing agent (e.g., methylcellulose (MC), ethyl cellulose, hydroxymethylcellulose, hydroxyethylcellulose (HEC), hydroxypropylcellulose (HPC), hydroxypropylmethylcellulose (HPMC), or a mixture thereof), or an in-package-coatingmaterial; sterilization such as autoclave at from 118 to 124° C. for atleast about 30 minutes; and the like.

Preferred surfaces treatments are LbL coating such as those described inU.S. Pat. Nos. 6,451,871, 6,719,929, 6,793,973, 6,811,805, and6,896,926, plasma treatment, in-package-coating such as those disclosedin U.S. Pat. Nos. 8,557,334, 8,529,057 and 9,505,184. A preferred plasmatreatment is those processes in which an ionized gas is applied to thesurface of an article as described in U.S. Pat. Nos. 4,312,575 and4,632,844.

The hydrogel contact lens is hydrated in water or an aqueous solution toreplace the liquid extraction medium, according to any method known to aperson skilled in the art.

The hydrated and/or surface-treated photochromic contact lens canfurther subject to further processes, such as, for example, packaging inlens packages with a packaging solution which is well known to a personskilled in the art; sterilization such as autoclave at from 118 to 124°C. for at least about 30 minutes; and the like.

Lens packages (or containers) are well known to a person skilled in theart for autoclaving and storing a soft contact lens. Any lens packagescan be used in the invention. Preferably, a lens package is a blisterpackage which comprises a base and a cover, wherein the cover isdetachably sealed to the base, wherein the base includes a cavity forreceiving a sterile packaging solution and the contact lens.

Lenses are packaged in individual packages, sealed, and sterilized(e.g., by autoclave at about 120° C. or higher for at least 30 minutesunder pressure) prior to dispensing to users. A person skilled in theart will understand well how to seal and sterilize lens packages.

A SiHy contact lens of the invention has an oxygen permeability ofpreferably at least about 40 barrers, more preferably at least about 60barrers, even more preferably at least about 80 barrers (at about 35°C.).

A hydrogel contact lens of the invention has an elastic modulus of about1.5 MPa or less, preferably about 1.2 MPa or less, more preferably fromabout 0.3 MPa to about 1.0 MPa (at a temperature of from about 22° C. to28° C.).

A hydrogel contact lens of the invention further has an equilibriumwater content of from about 15% to about 75%, more preferably from about20% to about 70% by weight, even more preferably from about 25% to about65% by weight (at room temperature) when fully hydrated. The equilibriumwater content of a photochromic contact lens can be measured accordingto the procedure disclosed in Example 1.

In a further aspect, the invention provides a hydrogel contact lensobtained by the method of the invention.

All of the various embodiments of the molds, polymerizable composition,and spatial limitation of radiation, and contact lens of the inventiondescribed above can be used in this aspect of the invention.

Although various embodiments of the invention have been described usingspecific terms, devices, and methods, such description is forillustrative purposes only. The words used are words of descriptionrather than of limitation. It is to be understood that changes andvariations may be made by those skilled in the art without departingfrom the spirit or scope of the present invention, which is set forth inthe following claims. In addition, it should be understood that aspectsof the various embodiments may be interchanged either in whole or inpart or can be combined in any manner and/or used together, asillustrated below:

-   1. A method for producing hydrogel contact lenses, comprising the    steps of:    -   (1) obtain a first polymerizable fluid composition and a second        polymerizable fluid composition, wherein the first polymerizable        fluid composition comprises at least one visible-light        free-radical photoinitiator, at least one thermal free-radical        initiator, at least one first polymerizable material, and at        least one photochromic compound, wherein the second        polymerizable fluid composition comprises said at least one        thermal free-radical initiator and at least one second        polymerizable material and is free of any photochromic compound,        wherein the first polymerizable fluid composition has a curing        time as determined in photo-rheology study using a visible light        at a specified intensity;    -   (2) obtaining a lens mold, wherein the lens mold comprises a        female mold half having a first molding surface defining the        anterior surface of a contact lens to be molded and a male mold        half having a second molding surface defining the posterior        surface of the contact lens to be molded, wherein the female and        male mold halves are configured to receive each other such that        a mold cavity is formed between the first and second molding        surfaces when the mold is closed;    -   (3) applying an amount of the first polymerizable fluid        composition onto a central zone of the first molding of the        female mold half to form a circular layer of the first        polymerizable fluid composition, wherein the circular layer has        a diameter of about 13.00 mm or less;    -   (4) actinically curing the circular layer of the first        polymerizable fluid composition to form a disk having curved        surfaces, wherein the step of actinically curing is carried out        by irradiating the circular layer of the first polymerizable        fluid composition with the visible light at the specified        intensity for at least 30% of the curing time;    -   (5) dispensing an amount of the second polymerizable fluid        composition over the partially-crosslinked circular layer on the        central zone of the first molding surface;    -   (6) closing the female mold half with the male mold half to form        a molding assembly comprising the partially crosslinked circular        layer immersed in the second polymerizable fluid composition        within the mold cavity;    -   (7) thermally curing the second polymerizable fluid composition        and the partially-crosslinked circular layer immersed therein in        the molding assembly to form an unprocessed hydrogel contact        lens having a central photochromic zone that has a diameter of        about 13 mm or less, is concentric with the central axis of the        unprocessed hydrogel contact lens;    -   (8) separating the molding assembly into the male and female        mold halves, with the unprocessed hydrogel contact lens adhered        onto a lens-adhered mold half which is one of the male and        female mold halves;    -   (9) removing the unprocessed hydrogel contact lens from the        lens-adhered mold half; and    -   (10) subjecting the unprocessed hydrogel contact lens to        post-molding processes including a hydration process and one or        more other processes selected from the group consisting of        extraction, surface treatment, packaging, sterilization, and        combinations thereof.-   2. The method of embodiment 1, wherein the first and second    polymerizable fluid compositions both are capable of forming a    non-silicone hydrogel, wherein said at least one first and second    polymerizable materials independent of each other are a first    monomer mixture comprising (a) at least one first hydrophilic    vinylic monomer and (b) at least one component selected from the    group consisting of at least one non-silicone vinylic crosslinker, a    non-silicone hydrophobic vinylic monomer, a UV-absorbing vinylic    monomer, and combinations thereof.-   3. The method of embodiment 2, wherein said at least one first    hydrophilic vinylic monomer comprises at least one    hydroxyl-containing vinylic monomer, N,N-dimethylarylamide,    N-vinylpyrrolidone, at least one methylene-containing pyrrolidone    monomer, or combinations thereof.-   4. The method of embodiment 2 or 3, wherein said at least one first    and second polymerizable materials independent of each other    comprises at least 50% by weight of at least one hydroxyl-containing    vinylic monomer, relative to the total weight of all polymerizable    materials present in the first polymerizable fluid composition.-   5. The method of embodiment 2 or 3, wherein said at least one first    and second polymerizable materials independent of each other    comprises at least 55% by weight of at least one hydroxyl-containing    vinylic monomer, relative to the total weight of all polymerizable    materials present in the first polymerizable fluid composition.-   6. The method of embodiment 2 or 3, wherein said at least one first    and second polymerizable materials independent of each other    comprises at least 60% by weight of at least one hydroxyl-containing    vinylic monomer, relative to the total weight of all polymerizable    materials present in the first polymerizable fluid composition.-   7. The method of embodiment 2 or 3, wherein said at least one first    and second polymerizable materials independent of each other    comprises at least 65% by weight of at least one hydroxyl-containing    vinylic monomer, relative to the total weight of all polymerizable    materials present in the first polymerizable fluid composition.-   8. The method of any one of embodiments 3 to 7, wherein said at    least one hydroxyl-containing vinylic monomer are selected from the    group consisting of 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl    (meth)acrylate, 2-hydroxypropyl (meth)acrylate, glycerol    methacrylate (GMA), di(ethylene glycol) (meth)acrylate, tri(ethylene    glycol) (meth)acrylate, tetra(ethylene glycol) (meth)acrylate,    poly(ethylene glycol) (meth)acrylate having a number average    molecular weight of up to 1500, trimethylammonium 2-hydroxy propyl    (meth)acrylate hydrochloride, N-2-hydroxylethyl (meth)acrylamide,    N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl    (meth)acrylamide, N-2,3-dihydroxypropyl (meth)acrylamide,    N-4-hydroxybutyl (meth)acrylamide, N,N-bis(2-hydroxyethyl)    (meth)acrylamide, N-tris(hydroxymethyl) methyl (meth)acrylamide,    N-2-hydroxyethyl vinyl carbamate, and combinations thereof.-   9. The method of any one of embodiments 3 to 7, wherein said at    least one hydroxyl-containing vinylic monomer are selected from the    group consisting of hydroxyethyl (meth)acrylate, glycerol    (meth)acrylate, N-2-hydroxyethyl (meth)acrylamide, N-3-hydroxypropyl    (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide,    N-2,3-dihydroxypropyl (meth)acrylamide, di(ethylene glycol)    (meth)acrylate, N-2-hydroxyethyl vinyl carbamate, and combinations    thereof.-   10. The method of any one of embodiments 3 to 7, wherein said at    least one hydroxyl-containing vinylic monomer are selected from the    group consisting of hydroxyethyl (meth)acrylate, glycerol    (meth)acrylate, N-2-hydroxyethyl (meth)acrylamide, and combinations    thereof.-   11. The method of embodiment 1, wherein the first and second    polymerizable fluid compositions both are capable of forming a    non-silicone hydrogel, wherein said at least one first and second    polymerizable materials independent of each other are a reactive    mixture comprising (a) one or more water-soluble non-silicone    prepolymers and optionally (b) at least one component selected from    the group consisting of a hydrophilic vinylic monomer, a    non-silicone vinylic crosslinker, a non-silicone hydrophobic vinylic    monomer, a UV-absorbing vinylic monomer, and combinations thereof.-   12. The method of embodiment 11, wherein the one or more    water-soluble non-silicone prepolymers are water-soluble    actinically-crosslinkable poly(vinyl alcohol) prepolymers each of    which comprises (a1) at least 60% by mole of repeating units of

and (a2) repeating units of

in which: R₃ and R₅ independent of each other are H or C₁-C₄ alkyl; R₄is a C₁-C₄ alkylene divalent radical; R₆ is a monovalent organic radicalhaving an acrylic group.

-   13. The method of embodiment 1, wherein the first and second    polymerizable fluid compositions both are capable of forming a    silicone hydrogel, wherein said at least one first and second    polymerizable materials independent of each other are a second    monomer mixture comprising (a) at least one silicone-containing    vinylic monomer, (b) at least one polysiloxane vinylic crosslinker,    at least one non-silicone vinylic crosslinker, or both, (c) at least    one second hydrophilic vinylic monomer, and optionally (d) at least    one component selected from the group consisting of a non-silicone    hydrophobic vinylic monomer, a UV-absorbing vinylic monomer, and    combinations thereof.-   14. The method of embodiment 13, wherein said at least one second    hydrophilic vinylic monomer comprises at least one hydrophilic    (meth)acrylamido monomer.-   15. The method of embodiment 14, wherein said at least one    hydrophilic (meth)acrylamido monomer having 3 to 8 carbon atoms    relative to the total weight of the polymerizable composition.-   16. The method of embodiment 14, wherein said at least one    hydrophilic (meth)acrylamido monomer is selected from the group    consisting of (meth)acrylamide, N-methyl (meth)acrylamide,    N,N-dimethyl (meth)acrylamide, N-ethyl (meth)acrylamide, N,N-diethyl    (meth)acrylamide, N-propyl (meth)acrylamide, N-isopropyl    (meth)acrylamide, N-3-methoxypropyl (meth)acrylamide,    N-2-hydroxylethyl (meth)acrylamide, N-3-hydroxypropyl    (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide,    N-2,3-dihydroxypropyl (meth)acrylamide, N-4-hydroxybutyl    (meth)acrylamide, N,N-bis(2-hydroxyethyl) (meth)acrylamide,    N-tris(hydroxymethyl) methyl (meth)acrylamide,    2-(meth)acrylamido-glycolic acid, 3-(meth)acrylamidopropionic acid,    4-(meth)acrylamido-butanoic acid,    3-(meth)acrylamido-2-methylbutanoic acid,    3-(meth)acrylamido-3-methylbutanoic acid,    2-(meth)acrylamido-2-methyl-3,3-dimethyl butanoic acid,    5-(meth)acrylamidopentanoic acid, 3-(meth)acrylamidohaxanoic acid,    4-(meth)acrylamido-3,3-dimethylhexanoic acid,    (3-(meth)acrylamidophenyl)boronic acid,    3-((3-methacrylamidopropyl)dimethylammonio)-propane-1-sulfonate;    3-((3-acrylamidopropyl)dimethylammonio)propane-1-sulfonate,    poly(ethylene glycol)ethyl (meth)acrylamide having a number average    molecular weight of up to 700, methoxy-poly(ethylene glycol)ethyl    (meth)acrylamide having a number average molecular weight of up to    700, and combinations thereof.-   17. The method of any one of embodiments 14 to 16, wherein said at    least one hydrophilic (meth)acrylamido monomer comprises    N,N-dimethyl (meth)acrylamide, N-ethyl (meth)acrylamide,    N-2-hydroxyethyl (meth)acrylamide, N-3-hydroxypropyl    (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide,    N-2,3-dihydroxypropyl (meth)acrylamide, (meth)acrylamide, or    combinations thereof.-   18. The method of any one of embodiments 14 to 16, wherein said at    least one hydrophilic (meth)acrylamido monomer comprises    N,N-dimethyl (meth)acrylamide, N-2-hydroxyethyl (meth)acrylamide, or    a combination thereof.-   19. The method of any one of embodiments 13 to 18, wherein said at    least one second hydrophilic vinylic monomer comprises at least one    hydrophilic (meth)acryloxy monomer.-   20. The method of embodiment 19, wherein said at least one second    hydrophilic (meth)acryloxy monomer is selected from the group    consisting of 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl    (meth)acrylate, 2-hydroxypropyl (meth)acrylate, glycerol    methacrylate (GMA), di(ethylene glycol) (meth)acrylate, tri(ethylene    glycol) (meth)acrylate, tetra(ethylene glycol) (meth)acrylate,    poly(ethylene glycol) (meth)acrylate having a number average    molecular weight of up to 1500, (meth)acrylic acid, ethylacrylic    acid, propylacrylic acid, butylacrylic acid, trimethylammonium    2-hydroxy propyl (meth)acrylate hydrochloride, dimethylaminoethyl    (meth)acrylate, ethylene glycol methyl ether (meth)acrylate,    di(ethylene glycol) methyl ether (meth)acrylate, tri(ethylene    glycol) methyl ether (meth)acrylate, tetra(ethylene glycol) methyl    ether (meth)acrylate, C₁-C₄-alkoxy poly(ethylene glycol)    (meth)acrylate having a number average molecular weight of up to    1500, and combinations thereof.-   21. The method of any one of embodiments 13 to 20, wherein said at    least one second hydrophilic vinylic monomer comprises at least one    hydrophilic N-vinyl amide monomer selected from the group consisting    of N-vinylpyrrolidone, N-vinyl-3-methyl-2-pyrrolidone,    N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone,    N-vinyl-6-methyl-2-pyrrolidone, N-vinyl-3-ethyl-2-pyrrolidone,    N-vinyl-4,5-dimethyl-2-pyrrolidone,    N-vinyl-5,5-dimethyl-2-pyrrolidone,    N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinyl piperidone (aka,    N-vinyl-2-piperidone), N-vinyl-3-methyl-2-piperidone,    N-vinyl-4-methyl-2-piperidone, N-vinyl-5-methyl-2-piperidone,    N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone,    N-vinyl-3,5-dimethyl-2-piperidone,    N-vinyl-4,4-dimethyl-2-piperidone, N-vinyl caprolactam (aka,    N-vinyl-2-caprolactam), N-vinyl-3-methyl-2-caprolactam,    N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam,    N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam,    N-vinyl-4,6-dimethyl-2-caprolactam,    N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methyl acetamide,    N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide,    N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, and mixtures    thereof.-   22. The method of any one of embodiments 13 to 20, wherein said at    least one second hydrophilic vinylic monomer comprises    N-vinylpyrrolidone and/or N-vinyl-N-methyl acetamide.-   23. The method of any one of embodiments 13 to 22, wherein said at    least one second hydrophilic vinylic monomer comprises: (a) at least    one methylene-containing pyrrolidone monomer selected from the group    consisting of 1-methyl-3-methylene-2-pyrrolidone,    1-ethyl-3-methylene-2-pyrrolidone,    1-methyl-5-methylene-2-pyrrolidone,    1-ethyl-5-methylene-2-pyrrolidone,    5-methyl-3-methylene-2-pyrrolidone,    5-ethyl-3-methylene-2-pyrrolidone,    1-n-propyl-3-methylene-2-pyrrolidone,    1-n-propyl-5-methylene-2-pyrrolidone,    1-isopropyl-3-methylene-2-pyrrolidone,    1-isopropyl-5-methylene-2-pyrrolidone,    1-n-butyl-3-methylene-2-pyrrolidone,    1-tert-butyl-3-methylene-2-pyrrolidone, and combinations    thereof; (b) at least one vinyl ether monomer selected from the    group consisting of ethylene glycol monovinyl ether, di(ethylene    glycol) monovinyl ether, tri(ethylene glycol) monovinyl ether,    tetra(ethylene glycol) monovinyl ether, poly(ethylene glycol)    monovinyl ether, ethylene glycol methyl vinyl ether, di(ethylene    glycol) methyl vinyl ether, tri(ethylene glycol) methyl vinyl ether,    tetra(ethylene glycol) methyl vinyl ether, poly(ethylene glycol)    methyl vinyl ether, and combinations thereof; (c) at least one allyl    ether monomer selected from the group consisting of ethylene glycol    monoallyl ether, di(ethylene glycol) monoallyl ether, tri(ethylene    glycol) monoallyl ether, tetra(ethylene glycol) monoallyl ether,    poly(ethylene glycol) monoallyl ether, ethylene glycol methyl allyl    ether, di(ethylene glycol) methyl allyl ether, tri(ethylene glycol)    methyl allyl ether, tetra(ethylene glycol) methyl allyl ether,    poly(ethylene glycol) methyl allyl ether, and combinations    thereof; (d) at least one phosphorylcholine-containing vinylic    monomer selected from the group consisting of (meth)acryloyloxyethyl    phosphorylcholine, (meth)acryloyloxypropyl phosphorylcholine,    4-((meth)acryloyloxy)butyl-2′-(trimethylammonio)ethylphosphate,    2-[(meth)acryloylamino]-ethyl-2′-(trimethylammonio)-ethylphosphate,    3-[(meth)acryloylamino]propyl-2′-(trimethylammonio)ethylphosphate,    4-[(meth)acryloylamino]butyl-2′-(trimethylammonio)-ethylphosphate,    5-((meth)acryloyloxy)pentyl-2′-(trimethylammonio)ethyl phosphate,    6-((meth)acryloyloxy)hexyl-2′-(trimethylammonio)-ethylphosphate,    2-((meth)acryloyloxy)-ethyl-2′-(triethylammonio)ethylphosphate,    2-((meth)acryloyloxy)ethyl-2′-(tripropylammonio)ethylphosphate,    2-((meth)acryloyloxy)ethyl-2′-(tributylammonio)ethyl phosphate,    2-((meth)acryloyloxy)propyl-2′-(trimethylammonio)-ethylphosphate,    2-((meth)acryloyloxy)butyl-2′-(trimethylammonio)ethylphosphate,    2-((meth)acryloyloxy)-pentyl-2′-(trimethylammonio)ethylphosphate,    2-((meth)acryloyloxy)hexyl-2′-(trimethylammonio)ethyl phosphate,    2-(vinyloxy)ethyl-2′-(trimethylammonio)-ethylphosphate,    2-(allyloxy)ethyl-2′-(trimethylammonio)ethylphosphate,    2-(vinyloxycarbonyl)ethyl-2′-(trimethylammonio)ethyl phosphate,    2-(allyloxycarbonyl)ethyl-2′-(trimethylammonio)-ethylphosphate,    2-(vinylcarbonylamino)ethyl-2′-(trimethylammonio)-ethylphosphate,    2-(allyloxycarbonylamino)ethyl-2′-(trimethylammonio)ethyl phosphate,    2-(butenoyloxy)ethyl-2′-(trimethylammonio)ethylphosphate, and    combinations thereof; (e) allyl alcohol; (f) N-2-hydroxyethyl vinyl    carbamate; (g) N-vinyloxycarbonyl-β-alanine (VINAL); (h)    N-vinyloxycarbonyl-α-alanine; or (i) combinations thereof.-   24. The method of any one of embodiment 13 to 23, wherein said at    least one silicone-containing vinylic monomer comprises at least one    silicone-containing (meth)acrylamido monomer containing a    tris(trialkylsiloxy)silyl group.-   25. The method of embodiment 24, wherein said at least one    silicone-containing (meth)acrylamido monomer containing a    tris(trialkylsiloxy)silyl group is selected from the group    consisting of N-[tris(trimethylsiloxy)silylpropyl] (meth)acrylamide,    N-[tris(dimethylethylsiloxy)-silylpropyl] (meth)acrylamide,    N-[tris(dimethylpropylsiloxy)silylpropyl] (meth)acrylamide,    N-[tris(dimethylphenylsiloxy)silylpropyl] (meth)acrylamide,    N-(2-hydroxy-3-(3-(tris(trimethyl-silyloxy)silyl)propyloxy)propyl)-2-methyl    (meth)acrylamide,    N-(2-hydroxy-3-(3-(tris(trimethyl-silyloxy)silyl)propyloxy)propyl)    (meth)acrylamide,    N,N-bis[2-hydroxy-3-(3-(tris(trimethyl-silyloxy)silyl)propyloxy)propyl]-2-methyl    (meth)acrylamide,    N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]    (meth)acrylamide, and combinations thereof.-   26. The method of any one of embodiments 13 to 25, wherein said at    least one silicone-containing vinylic monomer comprises at least one    silicone-containing (meth)acrylamido monomer containing a    bis(trialkylsilyloxy)-alkylsilyl group.-   27. The method of embodiment 26, wherein said at least one    silicone-containing (meth)acrylamido monomer containing a    bis(trialkylsilyloxy)alkylsilyl group is selected from the group    consisting of    N-(2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl)-2-methyl    (meth)acrylamide,    N-(2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)-propyl)    (meth)acrylamide,    N,N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)-propyloxy)propyl]-2-methyl    (meth)acrylamide,    N,N-bis[2-hydroxy-3-(3-(bis(trimethyl-silyloxy)methylsilyl)propyloxy)-propyl]    (meth)acrylamide,    N-[2-hydroxy-3-(3-(t-butyl-dimethylsilyl)propyloxy)propyl]-2-methyl    acrylamide, a siloxane-containing (meth)acrylamido monomer of one of    formula (Ia) to (Ih), and combinations thereof,

in which R₁₃ is a divalent alkylene radical of —CH₂CH₂—, —CH₂CH₂CH₂—,—CH₂CH₂CH₂CH₂—,

R₁₄ is a divalent alkylene radical of —CH₂CH₂— or —CH₂CH₂CH₂—, and R₁₅is a divalent alkylene radical of

R″ and R₁₁ independent of each other is C₁-C₄ alkyl, and f1 is aninteger of from 3 to 5.

-   28. The method of any one of embodiments 13 to 27, wherein said at    least one silicone-containing vinylic monomer comprises at least one    mono-(meth)acrylamido-terminated oligo- or polysiloxane of formula    (IIa)

-   -   in which R′ is hydrogen or methyl, R″ independent of each other        is C₁-C₆ alkyl, g1 and g2 independent of each other are integer        of 0 or 1, h1 is an integer of 2 to 25, R₉ and R₁₀ independent        of each other are a substituted or unsubstituted C₁-C₁₀ alkylene        divalent radical, Y₁ is a linkage of

in which R₁₂ and R₁₂′ independent of each other are C₁-C₆ alkyl.

-   29. The method of embodiment 28, wherein in formula (IIa) h1 is an    integer of 3 to 20 (more preferably 3 to 15).-   30. The method of embodiment 28 or 29, wherein in formula (IIa) R₁₂    and R₁₂′ independent of each other are methyl.-   31. The method of any one of embodiments 28 to 30, wherein at least    one mono-(meth)acrylamido-terminated oligo- or polysiloxane is    selected from the group consisting of    α-(meth)acryloyl-amidopropyloxypropyl terminated ω-C₁-C₄-alkyl    terminated polydimethylsiloxane,    α-N-methyl-(meth)acryloylamidopropyloxypropyl terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[3-(meth)acrylamidoethoxy-2-hydroxypropyloxy-propyl]-terminated    ω-C₁-C₄-alkyl polydimethylsiloxane,    α-[3-(meth)acrylamidopropyloxy-2-hydroxypropyloxy-propyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[3-(meth)acrylamido-isopropyloxy-2-hydroxypropyloxypropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[3-(meth)acrylamidobutyloxy-2-hydroxypropyloxy-propyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[3-(meth)acryloylamido-2-hydroxypropyloxypropyl] terminated    ω-C₁-C₄-alkyl polydimethylsiloxane,    α-[3-[N-methyl-(meth)acryloylamido]-2-hydroxypropyloxypropyl]terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    N-methyl-N′-(propyl-tetra(dimethylsiloxy)dimethylbutylsilane)    (meth)acrylamide,    N-(2,3-dihydroxypropane)-N′-(propyltetra(dimethylsiloxy)dimethyl-butylsilane)    (meth)acrylamide,    (meth)acryloylamido-propyltetra(dimethylsiloxy)-dimethylbutylsilane,    and combinations thereof.-   32. The method of any one of embodiments 13 to 31, wherein the    second monomer mixture comprises at least one polysiloxane vinylic    crosslinker selected from the group consisting of: an    α,ω-(meth)acryloxy-terminated polydimethylsiloxane; an    α,ω-(meth)acrylamido-terminated polydimethylsiloxane; an α,ω-vinyl    carbonate-terminated polydimethylsiloxane; an α,ω-vinyl    carbamate-terminated polydimethylsiloxane; a    bis-3-methacryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane; a    reaction product of glycidyl methacrylate with a    di-amino-functionalized polydimethylsiloxane; a reaction product of    an azlactone-containing vinylic monomer with a    di-hydroxyl-functionalized polydimethylsiloxane; and combinations    thereof.-   33. The method of any one of embodiments 13 to 31, wherein the    second monomer mixture comprises at least one polysiloxane vinylic    crosslinker of formula (H)

-   -   in which:    -   d1 is an integer of from 30 to 500 and d2 is an integer of from        1 to 75, provided that d2/d1 is from about 0.035 to about 0.15        (preferably from about 0.040 to about 0.12, even more preferably        from about 0.045 to about 0.10);    -   X_(h1) is O or NR_(hN) in which R_(hN) is hydrogen or        C₁-C₁₀-alkyl;    -   R_(h0) is hydrogen or methyl;    -   R_(h1) and R_(h2) independently of each other are a substituted        or unsubstituted C₁-C₁₀ alkylene divalent radical or a divalent        radical of —R_(h4)—O—R_(h5)— in which R_(h4) and R_(h5)        independently of each other are a substituted or unsubstituted        C₁-C₁₀ alkylene divalent radical;    -   R_(h3) is a monovalent radical of any one of formula (H-a) to        (H-e)

-   -   k1 is zero or 1; m1 is an integer of 2 to 4; m2 is an integer of        1 to 5; m3 is an integer of 3 to 6; m4 is an integer of 2 to 5;    -   R_(h6) is hydrogen or methyl;    -   R_(h7) is a C₂-C₆ hydrocarbon radical having (m2+1) valencies;    -   R_(h8) is a C₂-C₆ hydrocarbon radical having (m4+1) valencies;    -   R_(h9) is ethyl or hydroxymethyl;    -   R_(h10) is methyl or hydromethyl;    -   R_(h11) is hydroxyl or methoxy;    -   X_(h1) is a sulfur linkage of —S— or a teriary amino linkage of        —NR_(h12)— in which R_(h)12 is C₁-C₁ alkyl, hydroxyethyl,        hydroxypropyl, or 2,3-dihydroxypropyl; and    -   X_(h2) is a linkage of

in which R_(h13) is hydrogen or C₁-C₁₀ alkyl.

-   34. The method of any one of embodiments 13 to 31, wherein the    second monomer mixture comprises (i) at least one polysiloxane    vinylic crosslinker having one sole polydiorganosiloxane segment and    two terminal ethylenically-unsaturated groups selected from the    group consisting of (meth)acryloyloxy groups, (meth)acryloylamino    groups, vinyl carbonate groups, vinylcarbamate groups; and/or (ii)    at least one chain-extended polysiloxane vinylic crosslinker having    at least two polydiorganosiloxane segment and a covalent linker    between each pair of polydiorganosiloxane segments and two two    terminal ethylenically-unsaturated groups selected from the group    consisting of (meth)acryloyloxy groups, (meth)acryloylamino groups,    vinyl carbonate groups, vinylcarbamate groups.-   35. The method of any one of embodiments 13 to 31, wherein the    second monomer mixture comprises (i) at least one polysiloxane    vinylic crosslinker selected from the group consisting of    α,ω-bis[3-(meth)acrylamidopropyl]-terminated polydimethylsiloxane,    α,ω-bis[3-(meth)acryloxypropyl]-terminated polydimethylsiloxane,    α,ω-bis[3-(meth)acryloxy-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acryloxyethoxy-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acryloxy-propyloxy-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acryloxy-isopropyloxy-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acryloxybutyloxy-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acrylamidoethoxy-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acrylamidopropyloxy-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acrylamido-isopropyloxy-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acrylamidobutyloxy-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acryloxyethylamino-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acryloxypropylamino-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acryloxybutylamino-2-hydroxypropyloxy-propyl]-terminated    polydimethylsiloxane,    α,ω-bis[(meth)acrylamidoethylamino-2-hydroxypropyloxy-propyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acrylamido-propylamino-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[3-(meth)acrylamide-butylamino-2-hydroxypropyloxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[(meth)acryloxy-2-hydroxypropyloxy-ethoxypropyl]-terminated    polydimethylsiloxane,    α,ω-bis[(meth)acryloxy-2-hydroxypropyl-N-ethylaminopropyl]-terminated    polydimethylsiloxane,    α,ω-bis[(meth)acryloxy-2-hydroxypropyl-aminopropyl]-polydimethylsiloxane,    α,ω-bis[(meth)acryloxy-2-hydroxypropyloxy-(polyethylenoxy)propyl]-terminated    polydimethylsiloxane,    α,ω-bis[(meth)acryloxyethylamino-carbonyloxyethoxy-propyl]-terminated    polydimethylsiloxane,    α,ω-bis[(meth)acryloxyethylamino-carbonyloxy-(polyethylenoxy)propyl]-terminated    polydimethylsiloxane, and combinations thereof.-   36. The method of any one of embodiments 13 to 31, wherein the    second monomer mixture comprises at least one polysiloxane vinylic    crosslinker having a polymer chain segment (i.e., a divalent    radical) of

in which SN is an integer of 3 or larger and each of R_(S1) and R_(S2)independent of one another are selected from the group consisting of:C₁-C₁₀ alkyl; phenyl; C₁-C₄-alkyl-substituted phenyl;C₁-C₄-alkoxy-substituted phenyl; phenyl-C₁-C₆-alkyl; C₁-C₁₀ fluoroalkyl;C₁-C₁₀ fluoroether; aryl; aryl C₁-C₁₈ alkyl; -alk-(OC₂H₄)_(γ1)—OR^(o)(in which alk is C₁-C₆ alkylene diradical, R^(o) is H or C₁-C₄ alkyl andγ1 is an integer from 1 to 10); a C₂-C₄₀ organic radical having at leastone functional group selected from the group consisting of hydroxylgroup (—OH), carboxyl group (—COOH), amino linkages of —NR_(N1)—, amidelinkages of —CONR_(N1)—, amide of —CONR_(N1)R_(N1)′, urethane linkagesof —OCONH—, and C₁-C₄ alkoxy group, or a linear hydrophilic polymerchain, in which R_(N1) and R_(N1)′ independent of each other arehydrogen or a C₁-C₁₅ alkyl.

-   37. The method of any one of embodiments 13 to 31, wherein the    second monomer mixture comprises at least one polysiloxane vinylic    crosslinker of formula (1) or (2)

in which:

-   -   R_(o) is H or methyl;    -   υ1 is an integer of from 30 to 500; υ2 and υ3 independent of        each other are an integer of from 5 to 100; ω2 and ω3        independent of each other are an integer of from 1 to 15;    -   a1 and g1 independent of each other is zero or 1;    -   L₁ is a C₂-C₈ alkylene divalent radical or a divalent radical of        L₁′-X₁-L₁″-,

-   -   L₁′ is a C₂-C₈ alkylene divalent radical which has zero or one        hydroxyl group;    -   L₁″ is C₃-C₈ alkylene divalent radical which has zero or one        hydroxyl group;    -   L₂ is a divalent radical of

-   -   L₃ is a divalent radical of

in which PE is a divalent radical of

-   -   L₃′ is C₃-C₈ alkylene divalent radical;    -   R₂ is a C₄-C₁₄ hydrocarbon divalent radical;    -   R₃ is a C₂-C₆ alkylene divalent radical;    -   X_(o), X₁′, and X_(o1) independent of one another are O or NR₁;    -   X₁ is O, NR₁, NHCOO, OCONH, CONR₁, or NR₁CO;    -   Z₀ is a direct bond or a C₁-C₁₂ alkylene divalent radical.

-   38. The method of any one of embodiments 13 to 37, wherein the    second monomer mixture comprises at least one silicone-containing    vinylic monomer of formula (M1) or (M2):

-   -   in which: a_(M1) is zero or 1; R_(M0) is H or methyl; X_(M0) is        O or NR_(M1); L_(M1) is a C₂-C₈ alkylene divalent radical or a        divalent radical of -L_(M1)′-X_(M1)-L_(M1)″-,

L_(M1)′ is a C₂-C₈ alkylene divalent radical which has zero or onehydroxyl group; L_(M1)″ is C₃-C₈ alkylene divalent radical which haszero or one hydroxyl group; X_(M1) is O, NR_(M1), NHCOO, OCONH,CONR_(M1), or NR_(M1)CO; R_(M1) is H or a C₁-C₄ alkyl having 0 to 2hydroxyl group; R_(t1) and R_(t2) independent of each other are a C₁-C₆alkyl; X_(M1)′ is O or NR₁; v1 is an integer of 1 to 30; v2 is aninteger of 0 to 30; n1 is an integer of 3 to 40; and r1 is an integer of2 or 3.

-   39. The method of embodiment 38, wherein said at least one    silicone-containing vinylic monomer comprises    tris(trimethylsilyloxy)silylpropyl (meth)acrylate,    [3-(meth)acryloxy-2-hydroxypropyloxy]propylbis(trimethylsiloxy)methylsilane,    [3-(meth)acryloxy-2-hydroxypropyloxy]propylbis(trimethylsiloxy)butylsilane,    3-(meth)acryloxy-2-(2-hydroxyethoxy)propyloxy)propylbis(trimethylsiloxy)methylsilane,    3-(meth)acryloxy-2-hydroxypropyloxy)propyltris(trimethylsiloxy)silane,    N-2-(meth)acryloxyethyl-O-(methyl-bis-trimethylsiloxy-3-propyl)silyl    carbamate, 3-(trimethylsilyl)propylvinyl carbonate,    3-(vinyloxycarbonylthio)propyltris(trimethylsiloxy)silane,    3-[tris(trimethylsiloxy)silyl]-propylvinyl carbamate,    3-[tris(trimethylsiloxy)silyl] propyl allyl carbamate,    3-[tris(trimethylsiloxy)silyl]-propyl vinyl carbonate, or a    combination thereof.-   40. The method of any one of embodiments 13 to 37, wherein the    second monomer mixture comprises at least one silicone-containing    vinylic monomer selected from the group consisting of    α-(meth)acryloxypropyl terminated ω-C₁-C₄-alkyl terminated    polydimethylsiloxane, α-(meth)acryloxy-2-hydroxypropyloxypropyl    terminated ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-(2-hydroxyl-methacryloxypropyloxypropyl)-ω-C₁-C₄-alkyl-decamethylpentasiloxane,    α-[3-(meth)acryloxyethoxy-2-hydroxypropyloxypropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[3-(meth)acryloxy-propyloxy-2-hydroxypropyloxypropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[3-(meth)acryloxyisopropyloxy-2-hydroxypropyloxypropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[3-(meth)acryloxybutyloxy-2-hydroxypropyloxypropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[3-(meth)acryloxyethylamino-2-hydroxypropyloxypropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[3-(meth)acryloxypropylamino-2-hydroxypropyloxypropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[3-(meth)acryloxy-butylamino-2-hydroxypropyloxypropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-(meth)acryloxy-(polyethylenoxy)-2-hydroxypropyloxypropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[(meth)acryloxy-2-hydroxypropyloxy-ethoxypropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[(meth)acryloxy-2-hydroxypropyl-N-ethylaminopropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[(meth)acryloxy-2-hydroxypropyl-aminopropyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane,    α-[(meth)acryloxy-2-hydroxypropyloxy-(polyethylenoxy)propyl]-terminated    ω-C₁-C₄-alkyl terminated polydimethylsiloxane, α-vinyl    carbonate-terminated w-C₁-C₄-alkyl-terminated polydimethylsiloxanes,    α-vinyl carbamate-terminated ω-C₁-C₄-alkyl-terminated    polydimethylsiloxane, or a mixture thereof.-   41. The method of any one of embodiments 13 to 40, wherein the sum    of the amounts of components (a), (b) and (c) in the second monomer    mixture is at least about 60% by weight relative to the total weight    of all polymerizable materials present in the second monomer    mixture.-   42. The method of any one of embodiments 13 to 40, wherein the sum    of the amounts of components (a), (b) and (c) in the second monomer    mixture is at least about 65% by weight relative to the total weight    of all polymerizable materials present in the second monomer    mixture.-   43. The method of any one of embodiments 13 to 40, wherein the sum    of the amounts of components (a), (b) and (c) in the second monomer    mixture is at least about 70% by weight relative to the total weight    of all polymerizable materials present in the second monomer    mixture.-   44. The method of any one of embodiments 13 to 40, wherein the sum    of the amounts of components (a), (b) and (c) in the second monomer    mixture is at least about 75% by weight relative to the total weight    of all polymerizable materials present in the second monomer    mixture.-   45. The method of any one of embodiments 1 to 44, wherein said at    least one first and second polymerizable materials independent of    each other comprises at least one non-silicone vinylic crosslinker.-   46. The method of any one of embodiments 1 to 44, wherein said at    least one first and second polymerizable materials independent of    each other comprises at least one non-silicone vinylic crosslinker    selected from the group consisting of ethyleneglycol    di-(meth)acrylate, diethyleneglycol di-(meth)acrylate,    triethyleneglycol di-(meth)acrylate, tetraethyleneglycol    di-(meth)acrylate, glycerol di-(meth)acrylate, 1,3-propanediol    di-(meth)acrylate, 1,3-butanediol di-(meth)acrylate, 1,4-butanediol    di-(meth)acrylate, glycerol 1,3-diglycerolate di-(meth)acrylate,    ethylenebis[oxy(2-hydroxypropane-1,3-diyl)] di-(meth)acrylate,    bis[2-(meth)acryloxyethyl] phosphate, trimethylolpropane    di-(meth)acrylate, and 3,4-bis[(meth)acryloyl]tetrahydrofuan,    diacrylamide (i.e., N-(1-oxo-2-propenyl)-2-propenamide),    dimethacrylamide (i.e.,    N-(1-oxo-2-methyl-2-propenyl)-2-methyl-2-propenamide),    N,N-di(meth)acryloyl-N-methylamine,    N,N-di(meth)acryloyl-N-ethylamine, N,N′-methylene    bis(meth)acrylamide, N,N′-ethylene bis(meth)acrylamide,    N,N′-dihydroxyethylene bis(meth)acrylamide, N,N′-propylene    bis(meth)acrylamide, N,N′-2-hydroxypropylene bis(meth)acrylamide,    N,N′-2,3-dihydroxybutylene bis(meth)acrylamide,    1,3-bis(meth)acrylamide-propane-2-yl dihydrogen phosphate (i.e.,    N,N′-2-phophonyloxypropylene bis(meth)acrylamide), piperazine    diacrylamide (or 1,4-bis(meth)acryloyl piperazine),    tetraethyleneglycol divinyl ether, triethyleneglycol divinyl ether,    diethyleneglycol divinyl ether, ethyleneglycol divinyl ether,    triallyl isocyanurate, triallyl cyanurate, trimethylopropane    trimethacrylate, pentaerythritol tetramethacrylate, bisphenol A    dimethacrylate, and combinations thereof.-   47. The method of any one of embodiments 1 to 44, wherein said at    least one first and second polymerizable materials independent of    each other comprises at least one non-silicone vinylic crosslinker    selected from the group consisting of tetra(ethyleneglycol)    di-(meth)acrylate, tri(ethyleneglycol) di-(meth)acrylate,    ethyleneglycol di-(meth)acrylate, di(ethyleneglycol)    di-(meth)acrylate, tetraethyleneglycol divinyl ether,    triethyleneglycol divinyl ether, diethyleneglycol divinyl ether,    ethyleneglycol divinyl ether, triallyl isocyanurate, triallyl    cyanurate, or a combination thereof.-   48. The method of any one of embodiments 1 to 47, wherein said at    least one first and second polymerizable materials independent of    each other comprises at least one non-silicone hydrophobic vinylic    monomer.-   49. The method of any one of embodiments 1 to 47, wherein said at    least one first and second polymerizable materials independent of    each other comprises at least one C₁-C₈ alkyl (meth)acrylate, at    least one C₅-C₁₆ cycloalkyl (meth)acrylate, at least one aryl    methacrylate, (meth)acrylonitrile, at least one fluorine-containing    acrylic monomer, at least one vinyl alkanoate, at least one    vinyloxyalkane, at least one substituted or unsubstituted styrene,    vinyl toluene, vinyl chloride, vinylidene chloride, 1-butene, or    combinations thereof.-   50. The method of embodiment 49, wherein said at least one vinyl    alkanoate is selected from the group consisting of vinyl acetate,    vinyl propionate, vinyl butyrate, vinyl valerate, and combinations    thereof, wherein said at least one vinyloxyalkane is selected from    the group consisting of vinyl ethyl ether, propyl vinyl ether,    n-butyl vinyl ether, isoputyl vinyl ether, cyclohexyl vinyl ether,    t-butyl vinyl ether, and combinations thereof, wherein said at least    one fluorine-containing acrylic monomer is selected from the group    consisting of 2,2,2-trifluoroethyl (meth)acrylate, tetrafluoropropyl    (meth)acrylate, hexafluoro-iso-propyl (meth)acrylate,    hexafluorobutyl (meth)acrylate, heptafluorobutyl (meth)acrylate,    octafluoropentyl (meth)acrylate, heptadecafluorodecyl    (meth)acrylate, pentafluorophenyl (meth)acrylate,    perfluorohexylethyl-thio-carbonyl-aminoethyl-methacrylate, and    combinations thereof.-   51. The method of any one of embodiments 1 to 47, wherein said at    least one first and second polymerizable materials independent of    each other comprises methyl methacrylate, ethyl methacrylate,    isopropyl methacrylate, sec-butyl methacrylate, tert-butyl    methacrylate, cyclohexyl methacrylate, isobornyl acrylate, isobornyl    methacrylate, phenyl methacrylate, 4-tert-butylstyrene,    2-methylstyrene, styrene, 4-ethoxystyrene, 2,4-dimethystyrene,    2,5-dimethylstyrene, 3,5-dimethylstyrene, or combinations thereof.-   52. The method of any one of embodiments 1 to 47, wherein said at    least one first and second polymerizable materials independent of    each other comprises methyl methacrylate, tert-butyl methacrylate,    cyclohexyl methacrylate, isobornyl acrylate, isobornyl methacrylate,    or combinations thereof.-   53. The method of any one of embodiments 1 to 47, wherein said at    least one first and second polymerizable materials independent of    each other comprises methyl methacrylate, tert-butyl methacrylate,    cyclohexyl methacrylate, or combinations thereof.-   54. The method of any one of embodiments 1 to 53, wherein said at    least one first and second polymerizable materials independent of    each other comprises at least one UV-absorbing vinylic monomer.-   55. The method of any one of embodiments 1 to 53, wherein said at    least one first and second polymerizable materials independent of    each other comprises    2-[2′-hydroxy-5′-(2-methacryloxyethyl)phenyl)]-2H-benzotriazole    (Norbloc).-   56. The method of any one of embodiments 1 to 55, wherein said at    least one photochromic compound comprises a naphthopyran, an    indeno-fused naphthopyran (i.e., indeno-naphthopyran), a    heterocyclic ring-fused naphthopyrian, a benzopyran, a    phenanthropyran, a quinopyran, a quinolinopyran, a    fluoroanthenopyran, an anthracene-fused pyran, a tetracene-fused    pyran, a spiro(benzindoline) naphthopyran, a    spiro(indoline)naphthopyran, a spiro(indoline)benzopyran, a    spiro(indoline)quinopyran, a spiro(indoline)pyran, a naphthoxazine,    a spirobenzopyran, a spirobenzothiopyran, a naphthacenedione, a    benzoxazine, a spirooxazine, a naphthoxazine, a    spiro(benzindoline)naphthoxazine, a spiro(indoline)naphthoxazine, a    spiro(indoline)pyrido-benzoxazine, a spiro(indoline)benzoxazine, a    spiro(benzindoline) benzoxazine, a    spiro(benzindoline)pyridobenzoxazine, a spiro(indoline)    fluoranthenoxazine, a spiro(indoline)-quinoxazine, a    spiropiperidine-naphthopyran, a piro(indoline)pyronobenzoxazinone, a    benzospiropyran, a naphthospiropyran, a    spirobenzoxazine-pyrrolopyridine, a    spironaphthoxazine-pyrrolopyrridine, a spiro-oxazepin-benzoxazine, a    spiro-oxazepin-naphthoxazine, a spiro(indoline) benzothiazoloxazine,    a spiro(indoline)benzopyrroloxazine, a    spiro(indoline)quinazolino-oxazine, a    spiro(indoline)-anthracenobenzoxazine, a benzofurobenzopyran, a    benzothienobenzopyran, a naphthofurobenzopyran, a benzopyrano-fused    naphthopyran, a spiro(isoindoline)-naphthoxazine, a    spiro(isoindoline)benzoxazine, or a mixture thereof.-   57. The method of any one of embodiments 1 to 56, wherein said at    least one photochromic compound is polymerizable (i.e., comprising    an ethylenically-unsaturated group).-   58. The method of embodiment 57, wherein said at least one    photochromic compound is a coupling reaction product of a reactive    (meth)acrylamido or (meth)acryloxy monomer having a first reactive    functional group and a reactive photochromic compound have a second    reactive functional group in the absence or presence of a coupling    agent under coupling reaction, wherein the first reactive functional    group is selected from the group consisting of —COCl, —COBr, —COOH,    —NHR_(N2), —NCO, —OH, —CHO,

wherein the second reactive functional group is selected from the groupconsisting of —COOH, —NHR_(N2),

—NCO, —OH, —SH, —CHO,

wherein R₀ is hydrogen or methyl and R_(N2) is hydrogen, a linear orbranched C₁-C₁₅ alkyl, cyclohexyl, cyclopentyl, a substituted orunsubstituted phenyl, or a substituted- or unsubstituted-phenyl-C₁-C₆alkyl.

-   59. The method of embodiment 58, wherein the reactive    (meth)acrylamido or (meth)acryloxy monomer is selected from the    group consisting of (meth)acryloyl halides (CH₂═CH—COX or    CH₂═CCH₃—COX, X═Cl or Br), N-hydroxysuccinimide ester of    (meth)acrylic acid, glycidyl (meth)acrylate, isocyanato-C₂-C₆ alkyl    (meth)acrylate, amino-C₂-C₆ alkyl (meth)acrylamide, C₁-C₆    alkylamino-C₂-C₆ alkyl (meth)acrylamide, (meth)acrylic acid, C₂-C₄    alkylacrylic acid (e.g., ethylacrylic acid, propylacrylic acid,    butylacrylic acid), N-2-acrylamidoglycolic acid,    3-(acryloylxy)propanoic acid, C₂-C₆ hydroxylalkyl (meth)acrylate,    C₂-C₆ hydroxyalkyl (meth)acrylamide, azlactone-containing vinylic    monomers (e.g., 2-vinyl-4,4-dimethyl-1,3-oxazolin-5-one,    2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one,    2-vinyl-4-methyl-4-ethyl-1,3-oxazolin-5-one,    2-isopropenyl-4-methyl-4-butyl-1,3-oxazolin-5-one,    2-vinyl-4,4-dibutyl-1,3-oxazolin-5-one,    2-isopropenyl-4-methyl-4-dodecyl-1,3-oxazolin-5-one,    2-isopropenyl-4,4-diphenyl-1,3-oxazolin-5-one,    2-isopropenyl-4,4-pentamethylene-1,3-oxazolin-5-one,    2-isopropenyl-4,4-tetramethylene-1,3-oxazolin-5-one,    2-vinyl-4,4-diethyl-1,3-oxazolin-5-one,    2-vinyl-4-methyl-4-nonyl-1,3-oxazolin-5-one,    2-isopropenyl-4-methyl-4-phenyl-1,3-oxazolin-5-one,    2-isopropenyl-4-methyl-4-benzyl-1,3-oxazolin-5-one,    2-vinyl-4,4-pentamethylene-1,3-oxazolin-5-one, and    2-vinyl-4,4-dimethyl-1,3-oxazolin-6-one, with    2-vinyl-4,4-dimethyl-1,3-oxazolin-5-one (VDMO) and    2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one (IPDMO) as preferred    azlactone-containing vinylic monomers), aziridinyl C₁-C₁₂ alkyl    (meth)acrylate (e.g., 2-(1-aziridinyl) ethyl (meth)acrylate,    3-(1-aziridinyl) propyl (meth)acrylate, 4-(1-aziridinyl) butyl    (meth)acrylate, 6-(1-aziridinyl) hexyl (meth)acrylate, or    8-(1-aziridinyl) octyl (meth)acrylate), acrolein, methacrolein,    crotonaldehyde, and combinations thereof.-   60. The method of embodiment 58 or 59, wherein the reactive    photochromic compound comprises    3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-hydroxyethoxy-13-phenyl-3H,13H-indeno    [2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-(2-hydroxycarbonylethyl)carboxyethoxy-13-phenyl-3H,13H-indeno    [2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-hydroxy-13-phenyl-3H,13H-indeno    [2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-(2-hydroxycarbonylethyl)carboxy-13-phenyl-3H,13H-indeno    [2′,3′:3,4] naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-hydroxy-13-propyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-(2-hydroxycarbonylethyl)carboxy-13-propyl-3H,13H-indeno[2′,3′:3,4]-naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13-(2-hydroxycarbonylethyl)carboxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-7-methoxy-11-phenyl-13-hydroxymethyl-13-methyl-3H,13H-indeno[2′,3′:3,4]    naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-7-methoxy-11-phenyl-13-(2-hydroxycarbonylethyl)carboxymethyl-13-methyl-3H,13H-indeno[2′,3′:3,4]-naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-7-methoxy-11-phenyl-13-hydroxy-13-methyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-7-methoxy-11-phenyl-13-(2-hydroxycarbonylethyl)carboxy-13-methyl-3H,13H-indeno-[2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-11-phenyl-13-hydroxy-13-methyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-11-phenyl-13-(2-hydroxycarbonylethyl)carboxy-13-methyl-3H,13H-indeno[2′,3′:3,4]-naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-6,7,10,11-tetramethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-6,7,10,11-tetramethyl-13-(2-hydroxycarbonylethyl)carboxy-13-methyl-3H,13H-indeno[2′,3′:3,4]-naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-6,7-dimethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-11-(4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-6-methoxy-7-(3-hydroxymethylenepiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;    3,3-di(4-methoxyphenyl)-6-methoxy-7-(3-(2-hydroxycarbonylethyl)-carboxymethylenepiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;    3,3-di(4-methoxyphenyl)-6,7-dimethoxy-13-hydroxy-13-butyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-6,11,13-trimethyl-13-(2-(2-hydroxyethoxy)-ethoxy)-indeno[2,1-f]naptho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-6,11,13-trimethyl-13-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)-indeno[2,1-f]naptho[1,2-b]pyran;    3,3-diphenyl-13-hydroxy-13-(2-oxo-2-ethoxyethyl)-1H-indeno[2,1-f]naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-6,11-dimethyl-13-hydroxy-13-(2-oxo-2-ethoxyethyl)-1H-indeno[2,1-f]naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-6,11-dimethyl-13-butyl-13-hydroxy-indeno[2,1-f]naphtho[1,2-b]pyran;    3,3-bis(4-hydroxyphenyl)-7-methoxy-11-phenyl-13,13-diethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-hydroxyphenyl)-7-methoxy-11-phenyl-13,13-dipropyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-hydroxyphenyl)-7-methoxy-11-phenyl-13-carbomethoxy-13-methyl-3H,13H-indeno[2′,3′:3,4]    naphtho[1,2-b]pyran;    3,3-diphenyl-6,7-dimethoxy-13-methyl-13-methyl-13-hydroxyethoxy-ethoxyethoxy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-diphenyl-6,7,10,11-tetramethoxy-13-ethyl-13-methyl-13-hydroxyethoxyethoxy-3H,13H-indeno[2′,3′:3,4]naphtho    [1,2-b]pyran;    6,7-dimthoxy-2,2-diphenyl-13-hydroxy-13-butyl-2H,13H-indeno[1′,2′:4,3]    naphtho[1,2-b]pyran;    6,7-dimthoxy-2,2-diphenyl-13-hydroxy-13-methyl-2H,13H-indeno[1′,2′:4,3]naphtho[1,2-b]pyran;    6,7-dimthoxy-2,2-diphenyl-13-hydroxy-2H,13H-indeno[1′,2′:4,3]naphtho[1,2-b]pyran;    3-(4-allyloxyphenyl)-3-(4-morpholinophenyl)-7-methoxy-11-phenyl-13,13-dimethy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-(4-fluorophenyl)-3-(4-butoxyphenyl)-10-(piperazin-1-yl)-6-trifluoromethyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3:4]naphtho[1,2-b]pyran;    3-(4-fluorophenyl)-3-(4-butoxyphenyl)-10-(4-hydroxybenzamido)-6-trifluoromethyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3:4]naphtho[1,2-b]pyran;    3-(4-fluorophenyl)-3-(4-butoxyphenyl)-10-vinyl-6-trifluoromethyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3:4]naphtho[1,2-b]pyran;    3-(4-fluorophenyl)-3-(4-butoxyphenyl)-10-(carboxylic    acid)-6-trifluoromethyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3:4]naphtho[1,2-b]pyran;    3-(4-fluorophenyl)-3-(4-methoxyphenyl)-6-methoxy-7-(4-hydroxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-(4-fluorophenyl)-3-(4-methoxyphenyl)-6-methoxy-7-(4-(2-hydroxycarbonylethyl)    carboxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-(4-fluorophenyl)-3-(4-morpholinophenyl)-6-methoxy-7-(4-hydroxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;    3-(4-fluorophenyl)-3-(4-morpholinophenyl)-6-methoxy-7-(4-(2-hydroxycarbonylethyl)    carboxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]    naphtho[1.2-b]pyran;    3-(4-hydroxyethoxyphenyl)-3-(4-methoxyphenyl)-11-(4-(N,N-dimethylamino)phenyl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-(2,4-dimethoxyphenyl)-phenyl-6,11-dimethoxy-13-methyl-13-methyl-13-hydroxyethoxyethoxyethoxy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-(3-methyl-4-methoxyphenyl)-13-hydroxy-indeno[2,1-f]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-6,7,10,11-tetramethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-6,7,10,11-tetramethoxy-13-hydroxy-13-butyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-6,7-dimethoxy-13-hydroxy-13-ethyl-3H,13H-indeno    [2,1-f]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-6,7-dimethoxy-13-hydroxy-13-methyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-13-oxo-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-phenyl-6-methoxy-7-mprphlino-13-methyl-13-methyl-13-hydroxyethoxyethoxyethoxy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-phenyl-6,11-dimethoxy-13-methyl-13-methyl-13-hydroxyethoxy-ethoxy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    2-(4-methoxyphenyl)-2-(4-morpholinophenyl)-5-hydroxy-6-carboethoxy-2H-naphtho[1,2-b]    pyran;    3-(4-morpholinophenyl)-3-phenyl-6,7-dimethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3-(4-morpholinophenyl)-3-phenyl-6,7-dimethoxy-13-hydroxy-13-butyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3-(4-morpholinophenyl)-3-phenyl-6,7-dimethoxy-13-oxo-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;    3-phenyl-3-(4-hydroxyethoxyphenyl)-6-methoxy-7-morpholino-13,13-dimethyl-3H,13H-indeno-[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-(2-hydroxycarbonylethyl)carboxyethoxy-phenyl)-6-methoxy-7-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-(2-hydroxyethoxy)phenyl)-6-methoxy-7-piperidino-13,13-dimethy-3H,13H-indene[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-(2-(2-hydroxycarbonylethyl)-carboxyethoxy)phenyl)-6-methoxy-7-piperidino-13,13-dimethy-3H,13H-indene[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-hydroxyphenyl)-6,7-dimethoxy-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-hydroxyethoxy)phenyl)-6,7-dimethoxy-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]-naphtho[1,2-b]pyran;    3-phenyl-3-(4-(2-hydroxycarbonylethyl)carboxyethoxy)phenyl)-6,7-dimethoxy-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-(2-hydroxycarbonylethyl)carboxy-phenyl)-6,7-dimethoxy-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-(4-(2-(2-hydroxycarbonylethyl)-carboxyethyl)piperazin-1-yl)phenyl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;    3-phenyl-3-(4-methoxyphenyl)-6-methoxy-7-piperazinyl-13,13-dimethyl-3H,13H-indene[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-methoxyphenyl)-6-methoxy-7-(3-hydroxymethylenepiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno    [2′,3″:3.4]naphtho[1.2-b]pyran;    3-phenyl-3-(4-methoxyphenyl)-6-methoxy-7-(3-(2-hydroxycarbonylethyl)    carboxymethylenepiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3″:3.4]naphtho[1.2-b]pyran;    3-phenyl-3-(4-methoxyphenyl)-6-methoxy-7-(4-hydroxypipendin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;    3-phenyl-3-(4-methoxyphenyl)-6-methoxy-7-(4-(2-hydroxycarbonylethyl)-carboxypipendin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-(4-methoxyphenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-hydroxy-indeno    [2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-(4-methoxyphenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(2-hydroxy-2-methyl-3-butyn-4-yl)-indeno[2′,3′:3,4]naphtho    [1,2-b]pyran;    3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-(3-hydroxymethylene-piperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;    3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-(3-(2-hydroxycarbonyl-ethyl)carboxymethylene-piperidin-1-yl)-13,13-dimethyl-3H,13H-indeno    [2′,3′:3.4]-naphtho[1,2-b]pyran;    3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-(3-(2-hydroxycarbonylethyl)carboxymethylene-piperidin-1-yl)-13,13-dimethyl-3H,13H-indeno    [2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-(4-hydroxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;    3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-(4-(2-hydroxycarbonylethyl)-carboxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]    naphtho[1.2-b]pyran;    3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-piperazinyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho    [1.2-b]pyran;    3-phenyl-3-(4-morpholinophenyl)-6,11-dimethyl-13-hydroxy-13-(1-oxo-methoxyprop-2-yl)-1H-indeno[2,1-f]naphtho[1,2-b]pyran;    3-phenyl-3-(4-(4-phenylpiperazino)-phenyl)-6-methoxy-7-(4-hydroxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]    naphtho[1.2-b]pyran;    3-phenyl-3-(4-(4-phenylpiperazino)phenyl)-6-methoxy-7-(4-(2-hydroxycarbonylethyl)    carboxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]    naphtho[1.2-b]pyran;    3-phenyl-3-(4-piperazinylphenyl)-6,11-dimethoxy-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;    3-phenyl-3-(4-piperazinylphenyl)-6-methoxy-7-piperidinyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-(3-methylpiperazin-1-yl)phenyl)-6-methoxy-7-(decahydroisoquinolin-2-yl)-11-tert-butyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-16-(ethoxycarnobyl)methyl-16-hydroxy-3,16-dihydrobenzofuro-[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3-phenyl-3-(4-methoxyphenyl)-16-(ethoxycarnobyl)-methyl-16-hydroxy-3,16-dihydrobenzofuro    [2″,3″:6′,7′]indeno-[3′,2′:4,3]naphtho[1,2-b]pyran;    3-phenyl-3-(4-morpholinophenyl)-16-(ethoxycarnobyl)-methyl-16-hydroxy-3,16-dihydrobenzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]    naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-dihydro-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho    [1,2-b]pyran; 3,3-di(4-methoxyphenyl)-16-hydroxy-16H-benzofuro    [2″,3″:6,7]indeno [3′,2′:4,3]naphtho-[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2″,3″:6,7]-indeno[3′,2′:4,3]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-(2,3-diydrobenzofur-5-yl)-13-hydroxy-13-methyl-indeno[2,1-f]naphtho[1,2-b]pyran;    3-(4-methoxyphenyl)-3-(2,3-dihydrobenzofur-5-yl)-6,11-difluoro-13-hydroxy-13-(1-oxo-methoxyprop-2-yl)-1H-indeno[2,1-f]naphtho[1,2-b]pyran,    or a mixture thereof.-   61. The method of embodiment 58 or 59, wherein the reactive    photochromic compound is    2,2-di(4-fluorophenyl)-5-hydroxycarbonyl-6-phenyl-9-methoxy-2H-naphtho[1,2-b]pyran;    2,2-bis(4-methylphenyl)-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;    2,2-bis(4-methoxy-phenyl)-5-methoxycarbonyl-6-hydroxy-[2H]-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-methoxyethoxycarbonyl-6-methyl-8-vinyl-2H-naphtho[1,2-b]pyran;    2,2-bis(4-methoxy-phenyl)-5-methoxyethoxycarbonyl-6-methyl-8-hydroxycarbonyl-2H-naphtho    [1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-(2-hydroxyethoxy)ethoxy-[2H]-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-phenyl-9-(2-hydroxyethoxy)-[2H]-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-methoxy-carbonyl-6-(4-(2-hydroxy-ethoxy)phenyl)-[2H]-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-diphenylmethylol-6-hydroxy-2H-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-diphenylmethylol-6-methoxy-2H-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-(2-hydroxyethoxylcarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-(2-(2-hydroxyethoxy)-ethoxycarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-(2-(2-(2-hydroxyethoxy)ethoxy)-ethoxycarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-(2-(2-(2-(2-hydroxyethoxy)ethoxy)-ethoxy)-ethoxycarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-hydroxymethyl-6-methyl-9-methoxy-2H-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-hydroxymethyl-6-phenyl-2H-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-hydroxymethyl-6-methoxy-2H-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-(3-aminophenyl)-2H-naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-2,5,7-trihydro-7-methylidine-5-oxo-furo-[3′,4′:3,4]naphtho[1,2-b]pyran;    2,2-bis(4-methoxyphenyl)-5-phenylthio-6-hydroxy-2H-naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-13-hydroxy-13-methyl-indeno[2,1-f]naphtho[1,2-b]pyran;    3,3-di(4-methoxyphenyl)-9-methoxycarbonyl-8-(2-hydroxyethoxy)ethoxy-[3H]-naptho[1,2-b]pyran;    2,2-diphenyl-5-hydroxycarbonyl-9-methoxy-2H-naphtho[1,2-b]pyran;    2,2-diphenyl-5-hydroxycarbonyl-8,9-dimethoxy-2H-naphtho[1,2-b]pyran;    2,2-diphenyl-5-hydroxy-6-carboethoxy-2H-naphtho[1,2-b]pyran;    2,2-diphenyl-5-hydroxy-6-morpholinocarbonyl-2H-naphtho[1,2-b]pyran;    2,2-diphenyl-5-hydroxy-6-carboethoxy-2H-naphtho[1,2-b]pyran;    2,2-diphenyl-5-hydroxy-6-carbomethoxy-9-methoxy-2H-naphtho[1,2-b]pyran;    2,2-diphenyl-5-hydroxy-6-morpholino-carbonyl-2H-naphtho[1,2-b]pyran;    2,2-diphenyl-5-methylol-6-(3-dimethylaminopropyl)-methylamino-2H-naphtho[1,2-b]pyran;    2,2-diphenyl-2,5,7-trihydro-7-methyliden-5-oxofuro-[3′,4′:3,4]naphtho[1,2-b]pyran;    2,2-spiroadamantylene-5-phenylthio-6-hydroxy-2H-naphtho[1,2-b]pyran;    2,2-diphenyl)-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;    2,2-spiro-admamtylene-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran,    3,3-diphenyl-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;    2,2,5-triphenyl-6-carboethoxy-2H-naphtho[1,2-b]pyran;    2,2,6-triphenyl-5-(2-(2-(2-(2-hydroxyethoxy)ethoxy)-ethoxy)ethoxy)carbonyl-[2H]-naphtho[1,2-b]pyran;    2,2,6-triphenyl-5-(2-(2-(2-oxiran-2-ylmethoxy)ethoxy)ethoxy)-ethoxycarbonyl)-[2H]-naphtho[1,2-b]pyran;    2-(4-methoxyphenyl)-2-(4-morpholinophenyl)-5-hydroxy-6-carboethoxy-2H-naphtho[1,2-b]pyran;    2-(4-methoxy-phenyl)-2-tert-butyl-5-methoxy-carbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;    2-(4-methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;    2-(4-(2-(2-hydroxyethoxy)ethoxy)-ethoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-methyl-9-methoxy-[2H]-naphtho[1,2-b]pyran;    2-(4-(2-(2-hydroxyethoxy)ethoxy)phenyl)-2-phenyl-5-methoxycarbonyl-6-(2-(2-methylprop-2-enoxyloxy)ethoxy)-[2H]-naphtho[1,2-b]pyran;    3-(4-(2-(2-hydroxyethoxy)-ethoxy)ethoxyphenyl)-3-phenyl-9-methoxycarbonyl-8-methoxy-[3H]-naptho[1,2-b]pyran;    2-(4-morpholinophenyl)-2-phenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;    2-(9-ethylcarbazol-2-yl)-2-phenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;    2-(9-phenylcarbazol-2-yl)-2-phenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;    2-(4-dimethylaminophenyl)-2-phenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;    3-(2-flurophenyl)-3-(4-methoxyphenyl-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;    3-(2-flurophenyl)-3-(4-methoxyphenyl-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;    3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;    3-(2,4,6-triflurophenyl)-3-(2,4,6-trimethoxy-1-naphthyl)-8-acetyl-9-carboniloyl-3H-naphtho[2,1-b]pyran;    3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-6-methoxy-12-hydroxymethyl-11-phenyl-3H-phenanthro[1,2-b]pyran;    5,5-bis(4-methoxyphenyl)-8-methylol-5H-fluorantheno[3,2-b]pyran; or    a mixture thereof.-   62. The method of embodiment 58 or 59, wherein the reactive    photochromic compound is    1-hydroxy-ethyl-3,3-dimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1-hydroxypropyl-3,3-dimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1-aminoethyl-3,3-dimethyl-5-chlorospiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1-hydroxyethyl-3,3-dimethyl-8′-methoxyspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1-(p-vinylphenyl)-3,3-dimethyl-5,6-dichlorospiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1,3,3-trimethyl-9′-hydroxy-spiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1,3,3-trimethyl-5′-hydroxymethylspiro-[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1,3,3-trimethyl-9′-aminospiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1,3,3-trimethyl-5-chloro-8′-hydroxyspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1-benzyl-3,3-dimethyl-9′-vinylbenzoyloxyspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1-benzyl-3,3-dimethyl-5′-hydroxymethylpiperidinospiro-naphthooxazine;    1,3,3-trimethyl-9′-hydroxyspiro[indoline-2,3′-[3H]-pyrido-[2,1-b][1,4]benzooxazine];    5-hydroxy-6′-cyano-1,3,3-trimethyl-spiro-[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    5-hydroxy-6′-phenylsulfonyl-1,3,3-trimethyl-spiro-[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    5′formyl-1,3,3-trimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine;    1,3-dihydro-6′-piperazino-1,3,3-trimethyl spiro [2H    indole-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine;    1,3-dihydro-6′-(4-hydroxyethyl)piperazino-1,3,3-trimethyl spiro [2H    indole-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine;    1,3-dihydro-9′-hydroxy-1,3,3-trimethyl spiro 92H    indole-2,3′-[3H]-naphtho[2,1-b][1,4] oxazine;    1,3,3,4,5-pentamethyl-9′-methoxycarbonyl-8′-hydroxy-spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine;    1,3,3,5,6-pentamethyl-9′-methoxycarbonyl-8′-hydroxy-spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine;    1-propyl-3,3,4,5-tetramethyl-9′-methoxycarbonyl-8′-hydroxy-spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine;    1-propyl-3,3,5,6-tetramethyl-9′-methoxycarbonyl-8′-hydroxy-spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine;    1-methoxyethyl-3,3-dimethyl-9′-allyloxycarbonyl-8′-chloroactoxy-spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine;    1-allyl-3,3-spirocyclohexyl-9′-benzyloxycarbonyl-8′-chloroactoxy-spiro[indoline-2,3′-[3H]naphth-[2,1-b][1,4]oxazine;    5-amino-1,3,3-trimethyl-spiro[indoline-2,3′-[3H]-pyrido[3,4-f][1,4]-benzoxazine;    6-hydroxy-1′,3′,3′,4′,5′-pentamethylspiro[2H-1,4-benzoxazine-2,2′-indoline];    6-hydroxy-1′,3′,3′,5′,6′-pentamethylspiro[2H-1,4-benzoxazine-2,2′-indoline];    5,7-dimethoxy-1′-hydroxy-carbonylethyl-3′,3′-dimethylspiro[2H-1,4-bezoxazine-2,2′-indoline];    7-methoxy-1′-hydroxy-ethyl-3′,3′-dimethylspiro[2H-1,4-bezoxazine-2,2′-indoline];    9′-hydroxy-1-methyl-spiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];    5-chloro-9′-hydroxy-1-methylspiro-[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];    8′-hydroxy-1-methylspiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];    8′-hydroxy-5-methoxy-1-methylspiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];    8′-hydroxy-1,4,5-trimethylspiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];    9′-hydroxy-1-isopropylspiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];    9′-hydroxy-1-hexadecyl-spiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];    9′-hydroxy-1-octadecylspiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];    1,1″-(1,5-pentanediyl)bis[3,3-dimethyl]-9′-hydroxy-spiro[indoline-2,3′-[3H]-naphtho[2,1-b]    [1,4]oxazine]; 1,1″-[1,4-phenylenebis(methylene)]    bis[3,3-dimethyl]-5′-hydroxymethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b]    [1,4]oxazine];    1,1″-(1,4-butanediyl)bis[5,6-dichloro-3,3-dimethyl]-8′-hydroxy-spiro[indoline-2,3′-[3H]-naphtho[2,1-b]    [1,4]oxazine];    1,3,3-trimethyl-9′-hydroxypiperidino-spironaphthooxazine;    3-carboxyethyl-1,1-dimethyl-9′-methoxy-spiro[benz[e]-indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1-carboxyethyl-3,3-dimethyl-9′-methoxyspiro[benz[g]-indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    1,1-dimethyl-3-hydroxyethyl-9′-methoxy-spiro[benz[e]-indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    3,3-dimethyl-1-hydroxyethyl-9′-methoxyspiro[benz[g]-indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    3-carboxyethyl-1,1-dimethyl-9′-methoxyspiro[benz[e]-indoline-2,3′-[3H]-pyrido[2,1-b][1,4]benzoxazine];    1-carboxyethyl-3,3-dimethyl-9′-methoxyspiro[benz[g]-indoline-2,3′-[3H]-pyrido[2,1-b][1,4]benzoxazine];    1,1-dimethyl-3-hydroxyethyl-9′-methoxyspiro[benz[e]-indoline-2,3′-[3H]-pyrido[2,1-b][1,4]benzoxazine];    3,3-dimethyl-1-hydroxyethyl-9′-methoxyspiro[benz[g]-indoline-2,3′-[3H]-pyrido[2,1-b][1,4]benzoxazine];    5-amino-5′-(2-benzthiazolyl)-1,3,3-trimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    5-amino-5′-(5′-(2-hydroxyphenyl)-2-oxadiazolyl)-1-isopropyl-3,3-dimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    5-amino-5′-(5′-phenyl-2-oxadiazolyl)-1,3,3-trimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];    or a mixture thereof.-   63. The method of embodiment 58 or 59, wherein the reactive    photochromic compound is    3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-hydroxyethoxy-13-phenyl-3H,13H-indeno    [2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-(2-hydroxycarbonylethyl)carboxyethoxy-13-phenyl-3H,13H-indeno    [2′,3′:3,4]naphtho[1,2-b]pyran;    3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-hydroxy-13-phenyl-3H,13H-indeno    [2′,3′:3,4]naphtho[1,2-b]pyran; or a mixture thereof.-   64. The method of any one of embodiments 1 to 63, wherein said at    least one first and second polymerizable materials independent of    each otehr comprises at least one polymerizable UV/HEVL-absorbing    compound.-   65. The method of any one of embodiments 1 to 66, wherein said at    least one visible light free radical initiator comprises a    benzoylphosphine initiator and/or an acylgermanium photoinitiator.-   66. The method of embodiment 65, wherein said at least one first    free radical initiator comprises an acylgermanium photoinitiator    that

-   67. The method of embodiment 67 or 68, wherein the visible light is    a visible light in a region of from 420 nm to 500 nm.-   68. The method of any one of embodiments 1 to 67, wherein the step    of actinically curing is carried out by irradiating the circular    layer of the first polymerizable fluid composition with the visible    light at the specified intensity for at least about 50% of the    curing time.-   69. The method of any one of embodiments 1 to 67, wherein the step    of actinically curing is carried out by irradiating the circular    layer of the first polymerizable fluid composition with the visible    light at the specified intensity for at least about 70% of the    curing time.-   70. The method of any one of embodiments 1 to 67, wherein the step    of actinically curing is carried out by irradiating the circular    layer of the first polymerizable fluid composition with the visible    light at the specified intensity for at least about 90% of the    curing time.-   71. A hydrogel contact lens obtained according to the method of any    one of embodiments 1 to 70.

The previous disclosure will enable one having ordinary skill in the artto practice the invention. Various modifications, variations, andcombinations can be made to the various embodiment described herein. Inorder to better enable the reader to understand specific embodiments andthe advantages thereof, reference to the following examples issuggested. It is intended that the specification and examples beconsidered as exemplary.

Example 1 Oxygen Permeability Measurements

Unless specified, the oxygen transmissibility (Dk/t), the intrinsic (oredge-corrected) oxygen permeability (Dk_(i) or Dk_(c)) of a lens and alens material are determined according to procedures described in ISO18369-4.

Equilibrium Water Content

The equilibrium water content (EWC) of contact lenses are determined asfollows.

Amount of water (expressed as percent by weight) present in a hydratedhydrogel contact lens, which is fully equilibrated in saline solution,is determined at room temperature.

Quickly stack the lenses, and transfer the lens stack to the aluminumpan on the analytical balance after blotting lens in a cloth. The numberof lenses for each sample pan is typically five (5). Record the pan plushydrated weight of the lenses. Cover the pan with aluminum foil. Placepans in a laboratory oven at 100±2° C. to dry for 16-18 hours. Removepan plus lenses from the oven and cool in a desiccator for at least 30minutes. Remove a single pan from the desiccator, and discard thealuminum foil. Weigh the pan plus dried lens sample on an analyticalbalance. Repeat for all pans. The wet and dry weight of the lens samplescan be calculated by subtracting the weight of the empty weigh pan.

Elastic Modulus

The elastic modulus of a contact lens is determined using a MTS insightinstrument. The contact lens is first cut into a 3.12 mm wide stripusing Precision Concept two stage cutter. Five thickness values aremeasured within 6.5 mm gauge length. The strip is mounted on theinstrument grips and submerged in PBS (phosphate buffered saline) withthe temperature controlled at 21±2° C. Typically 5N Load cell is usedfor the test. Constant force and speed is applied to the sample untilthe sample breaks. Force and displacement data are collected by theTestWorks software. The elastic modulus value is calculated by theTestWorks software which is the slope or tangent of the stress vs.strain curve near zero elongation, in the elastic deformation region.

Photo-rheology: The photo-rheology experiment measures the elastic (G′)and viscous modulus (G″) as a function of time during curing. Theexperiment is conducted by using an appropriate light source, optionallycutoff filters to select wavelengths of interest, and a rheometer. Forexample, a light source can be a blue light LEDs (CureBox 450-500 nm;total irradiance of 0.2-5 mW/cm²). The sample (i.e., a polymerizablecomposition) is placed between a quartz plate that allows the actinicradiation (i.e., the blue light) to pass through and the rheometer. Thecuring time of a polymerizable composition is determined when theelastic modulus (G′) reaches a plateau.

Chemicals

PrOH represent 1-propanol; EtOAc represents ethyl acetate; DMArepresents N,N-dimethylacrylamide; MMA represents methyl methacrylate;EGMA represents ethylene glycol methyl ether methacrylate; TEGDMArepresent triethyleneglycol dimethacrylate; D6 representsmonobutyl-terminated monomethacryloxypropyl-terminatedpolydimethylsiloxane (Mw ˜750 g/mol g/mol from Shin-Etsu); GA representsa hydrophilized polysiloxane vinylic crosslinker of formula (G) (Mn˜11.6K g/mol, OH content ˜2.1 meq/g from Shin-Etsu); Betacon representsa dimethacrylate-terminated chain-extended polydimethylsiloxane (Mn ˜5000 g/mol), which has two polydimethylsiloxane (PDMS) segmentsseparated by one perfluoropolyether (PFPE) via diurethane linkagesbetween PDMS and PFPE segments and two urethane linkages each locatedbetween one terminal methacrylate group and one PDMS segment, isprepared according to method similar to what described in Example B-1 ofU.S. Pat. No. 5,760,100; Ge—PI representsBis(4-methoxybenzoyl)diethylgermanium (an acylgermanium photoinitiator);Vazo 64 represents 2,2′-dimethyl-2,2′azodipropiononitrile; Nobloc is2-[3-(2H-Benzotriazol-2-yl)-4-hydroxyphenyl]ethyl methacrylate fromAldrich; Norbloc is2-[2′-hydroxy-5′-(2-methacryloxyethyl)phenyl)]-2H-benzotriazole fromAldrich; NPD-blue represent a polymerizable naphthopyran photochromicdye having a blue color in activated state (from Vivimed); NPD-greenrepresents a polymerizable naphthopyran photochromic dye having a greencolor in activated state (from Vivimed); RB247 is Reactive Blue 247.

Example 2 Polymerizable Compositions

Two polymerizable compositions for forming silicone hydrogel materialsare prepared by blending all the required components to have thecompositions shown in Tables 1 and 2.

TABLE 1 Component Formulation A (weight unit parts) D6 31 DMA 48 MMA 9EGMA 10.2 EtOAc 5 Norbloc 1.5 RB247 0.12 Vazo 64 1 NPD-blue 1.5NPD-green 2.5 Betacon 148 Ge-PI 1

TABLE 2 Component Formulation B (weight unit parts) TEGDMA 0.3 D6 31 GA15 DMA 22 MMA 9 EGMA 10.2 TAA 17 Norbloc 1.5 Vazo 64 0.5

Photo-Rheology Study

Photo-rheology data is acquired by curing Formulation 2A by using bluelight LEDs (CureBox 450-500 nm; total irradiance of 0.2 mW/cm²). Theresult is shown in FIG. 2.

Fabrication of SiHy Contact Lens with a Central Photochromic Zone

˜3 μL of Formulation 2A is dosed to the center of a female (FC) moldhalf (made of polypropylene) of a plastic mold (power: −3.0) to form acircular layer, and partially cured by blue light LED (CureBox 450-500nm; total irradiance of 0.2 mW/cm²) for one of the following times: 0(control); 1; 5; 8; and 13 minutes.

30-80 μL of Formulation 2B is added in the female (FC) mold half toimmerse the partially cured circular layer and then the mold is closedwith the male (BC) mold half to form a molding assembly comprisingFormulation 2B and the partially-cured circular layer immersed therein.

The molding assembly is thermally cured in an oven under the followingcuring profile: ramp from room temperature to 55° C. at a ramp rate ofabout 7° C./minute; holding at 55° C. for about 30 minutes; ramp from55° C. to 80° C. at a ramp rate of about 7° C./minute; holding at 80° C.for about 30 minutes; ramp from 80° C. to 100° C. at a ramp rate ofabout 7° C./minute; and holding at 100° C. for about 30 minutes.

After de-molding, cast-molded SiHy contact lenses are extracted withPrOH for 180 minutes and then rinsed in PB (phosphate buffer containingabout 0.077 wt. % NaH₂PO₄.H₂O and about 0.31 wt. % Na₂HPO₄.2H₂O) for 1hour.

Lenses are formed with a center region containing photochromic activity(5-8 mm). These areas can be activated with UVA (black light). For thecenter cured lenses, a progression of pronounced outer ridges isobserved on the center portion as curing time increases. This may be theresult of mechanical differences between the center and edge. Further,there is bleeding of photochromic material observed with lenses made inthe process free of photo-curing step, but there is no significantbleeding of photochromic material observed with lenses made in theprocess involving a step of photo-curing for a curing time of 1, 5 and 8minutes.

All the publications and patents which have been cited herein above arehereby incorporated by reference in their entireties.

What is claimed is:
 1. A method for producing hydrogel contact lenses,comprising the steps of: (1) obtain a first polymerizable fluidcomposition and a second polymerizable fluid composition, wherein thefirst polymerizable fluid composition comprises at least onevisible-light free-radical photoinitiator, at least one thermalfree-radical initiator, at least one first polymerizable material, andat least one photochromic compound, wherein the second polymerizablefluid composition comprises said at least one thermal free-radicalinitiator and at least one second polymerizable material and is free ofany photochromic compound, wherein the first polymerizable fluidcomposition has a curing time as determined in photo-rheology studyusing a visible light at a specified intensity; (2) obtaining a lensmold, wherein the lens mold comprises a female mold half having a firstmolding surface defining the anterior surface of a contact lens to bemolded and a male mold half having a second molding surface defining theposterior surface of the contact lens to be molded, wherein the femaleand male mold halves are configured to receive each other such that amold cavity is formed between the first and second molding surfaces whenthe mold is closed; (3) applying an amount of the first polymerizablefluid composition onto a central zone of the first molding of the femalemold half to form a circular layer of the first polymerizable fluidcomposition, wherein the circular layer has a diameter of about 13.00 mmor less; (4) actinically curing the circular layer of the firstpolymerizable fluid composition to form a disk having curved surfaces,wherein the step of actinically curing is carried out by irradiating thecircular layer of the first polymerizable fluid composition with thevisible light at the specified intensity for at least 30% of the curingtime; (5) dispensing an amount of the second polymerizable fluidcomposition over the partially-crosslinked circular layer on the centralzone of the first molding surface; (6) closing the female mold half withthe male mold half to form a molding assembly comprising the partiallycrosslinked circular layer immersed in the second polymerizable fluidcomposition within the mold cavity; (7) thermally curing the secondpolymerizable fluid composition and the partially-crosslinked circularlayer immersed therein in the molding assembly to form an unprocessedhydrogel contact lens having a central photochromic zone that has adiameter of about 13 mm or less, is concentric with the central axis ofthe unprocessed hydrogel contact lens; (8) separating the moldingassembly into the male and female mold halves, with the unprocessedhydrogel contact lens adhered onto a lens-adhered mold half which is oneof the male and female mold halves; (9) removing the unprocessedhydrogel contact lens from the lens-adhered mold half; and (10)subjecting the unprocessed hydrogel contact lens to post-moldingprocesses including a hydration process and one or more other processesselected from the group consisting of extraction, surface treatment,packaging, sterilization, and combinations thereof.
 2. The method ofclaim 1, wherein the first and second polymerizable fluid compositionsboth are capable of forming a non-silicone hydrogel, wherein said atleast one first and second polymerizable materials independent of eachother are a first monomer mixture comprising (a) at least one firsthydrophilic vinylic monomer selected from the group consisting of atleast one hydroxyl-containing vinylic monomer, N,N-dimethylarylamide,N-vinylpyrrolidone, at least one methylene-containing pyrrolidonemonomer, and combinations thereof, and (b) at least one componentselected from the group consisting of at least one non-silicone vinyliccrosslinker, a non-silicone hydrophobic vinylic monomer, a UV-absorbingvinylic monomer, and combinations thereof.
 3. The method of claim 2,wherein said at least one first and second polymerizable materialsindependent of each other comprises at least 50% by weight of at leastone hydroxyl-containing vinylic monomer, relative to the total weight ofall polymerizable materials present in the first polymerizable fluidcomposition.
 4. The method of claim 1, wherein the first and secondpolymerizable fluid compositions both are capable of forming anon-silicone hydrogel, wherein said at least one first and secondpolymerizable materials independent of each other are a reactive mixturecomprising (a) one or more water-soluble non-silicone prepolymers andoptionally (b) at least one component selected from the group consistingof a hydrophilic vinylic monomer, a non-silicone vinylic crosslinker, anon-silicone hydrophobic vinylic monomer, a UV-absorbing vinylicmonomer, and combinations thereof.
 5. The method of claim 1, wherein thefirst and second polymerizable fluid compositions both are capable offorming a silicone hydrogel, wherein said at least one first and secondpolymerizable materials independent of each other are a second monomermixture comprising (a) at least one silicone-containing vinylic monomer,(b) at least one polysiloxane vinylic crosslinker, at least onenon-silicone vinylic crosslinker, or both, (c) at least one secondhydrophilic vinylic monomer, and optionally (d) at least one componentselected from the group consisting of a non-silicone hydrophobic vinylicmonomer, a UV-absorbing vinylic monomer, and combinations thereof,wherein said at least one second hydrophilic vinylic monomer comprisesat least one hydrophilic (meth)acrylamido monomer having 3 to 8 carbonatoms, at least one hydrophilic (meth)acryloxy monomer, at least onehydrophilic N-vinyl amide monomer, at least one methylene-containingpyrrolidone monomer, at least one vinyl ether monomer, at least oneallyl ether monomer, at least one phosphorylcholine-containing vinylicmonomer, N-2-hydroxyethyl vinyl carbamate, N-vinyloxycarbonyl-β-alanine,N-vinyloxycarbonyl-α-alanine, or (i) combinations thereof, wherein saidat least one silicone-containing vinylic monomer comprises (i) at leastone silicone-containing vinylic monomer containing atris(trialkylsiloxy)silyl group and one sole ethylenically-unsaturatedgroup selected from the group consisting of a (meth)acryloyloxy group, a(meth)acryloylamino group, a vinyl carbonate group, and a vinylcarbamategroup; (ii) at least one silicone-containing vinylic monomer containinga bis(trialkylsilyloxy)-alkylsilyl group and one soleethylenically-unsaturated group selected from the group consisting of a(meth)acryloyloxy group, a (meth)acryloylamino group, a vinyl carbonategroup, and a vinylcarbamate group; (iii) at least silicone-containingvinylic monomer containing a) one sole ethylenically-unsaturated groupselected from the group consisting of a (meth)acryloyloxy group, a(meth)acryloylamino group, a vinyl carbonate group, and a vinylcarbamategroup and b) a polysiloxane chain having 2 to 30 siloxane units andterminated with an alkyl, hydroxyalkyl or methoxyalkyl group; or (iv)combinations thereof.
 6. The method of claim 5, wherein the secondmonomer mixture comprises at least one polysiloxane vinylic crosslinkerof formula (H)

in which: d1 is an integer of from 30 to 500 and d2 is an integer offrom 1 to 75, provided that d2/d1 is from about 0.035 to about 0.15(preferably from about 0.040 to about 0.12, even more preferably fromabout 0.045 to about 0.10); X_(h1) is O or NR_(hN) in which R_(hN) ishydrogen or C₁-C₁₀-alkyl; R_(h0) is hydrogen or methyl; R_(h1) andR_(h2) independently of each other are a substituted or unsubstitutedC₁-C₁₀ alkylene divalent radical or a divalent radical of—R_(h4)—O—R_(h5)— in which R_(h4) and R_(h5) independently of each otherare a substituted or unsubstituted C₁-C₁₀ alkylene divalent radical;R_(h3) is a monovalent radical of any one of formula (H-a) to (H-e)

k1 is zero or 1; m1 is an integer of 2 to 4; m2 is an integer of 1 to 5;m3 is an integer of 3 to 6; m4 is an integer of 2 to 5; R_(h6) ishydrogen or methyl; R_(h7) is a C₂-C₆ hydrocarbon radical having (m2+1)valencies; R_(h8) is a C₂-C₆ hydrocarbon radical having (m4+1)valencies; R_(h9) is ethyl or hydroxymethyl; R_(h10) is methyl orhydromethyl; R_(h11) is hydroxyl or methoxy; X_(h1) is a sulfur linkageof —S— or a teriary amino linkage of —NR_(h12)— in which R_(h12) isC₁-C₁ alkyl, hydroxyethyl, hydroxypropyl, or 2,3-dihydroxypropyl; andX_(h2) is a linkage of

in which R_(h13) is hydrogen or C₁-C₁₀ alkyl.
 7. The method of claim 5,wherein the second monomer mixture comprises (i) at least onepolysiloxane vinylic crosslinker having one sole polydiorganosiloxanesegment and two terminal ethylenically-unsaturated groups selected fromthe group consisting of (meth)acryloyloxy groups, (meth)acryloylaminogroups, vinyl carbonate groups, vinylcarbamate groups; and/or (ii) atleast one chain-extended polysiloxane vinylic crosslinker having atleast two polydiorganosiloxane segment and a covalent linker betweeneach pair of polydiorganosiloxane segments and two two terminalethylenically-unsaturated groups selected from the group consisting of(meth)acryloyloxy groups, (meth)acryloylamino groups, vinyl carbonategroups, vinylcarbamate groups.
 8. The method of claim 7, wherein the sumof the amounts of components (a), (b) and (c) in the second monomermixture is at least about 60% by weight relative to the total weight ofall polymerizable materials present in the second monomer mixture. 9.The method of claim 1, wherein said at least one first and secondpolymerizable materials independent of each other comprise: (i) at leastone non-silicone vinylic crosslinker selected from the group consistingof ethyleneglycol di-(meth)acrylate, diethyleneglycol di-(meth)acrylate,triethyleneglycol di-(meth)acrylate, tetraethyleneglycoldi-(meth)acrylate, glycerol di-(meth)acrylate, 1,3-propanedioldi-(meth)acrylate, 1,3-butanediol di-(meth)acrylate, 1,4-butanedioldi-(meth)acrylate, glycerol 1,3-diglycerolate di-(meth)acrylate,ethylenebis[oxy(2-hydroxypropane-1,3-diyl)] di-(meth)acrylate,bis[2-(meth)acryloxyethyl] phosphate, trimethylolpropanedi-(meth)acrylate, and 3,4-bis[(meth)acryloyl]tetrahydrofuan,diacrylamide (i.e., N-(1-oxo-2-propenyl)-2-propenamide),dimethacrylamide (i.e.,N-(1-oxo-2-methyl-2-propenyl)-2-methyl-2-propenamide),N,N-di(meth)acryloyl-N-methylamine, N,N-di(meth)acryloyl-N-ethylamine,N,N′-methylene bis(meth)acrylamide, N,N′-ethylene bis(meth)acrylamide,N,N′-dihydroxyethylene bis(meth)acrylamide, N,N′-propylenebis(meth)acrylamide, N,N′-2-hydroxypropylene bis(meth)acrylamide,N,N′-2,3-dihydroxybutylene bis(meth)acrylamide,1,3-bis(meth)acrylamide-propane-2-yl dihydrogen phosphate (i.e.,N,N′-2-phophonyloxypropylene bis(meth)acrylamide), piperazinediacrylamide (or 1,4-bis(meth)acryloyl piperazine), tetraethyleneglycoldivinyl ether, triethyleneglycol divinyl ether, diethyleneglycol divinylether, ethyleneglycol divinyl ether, triallyl isocyanurate, triallylcyanurate, trimethylopropane trimethacrylate, pentaerythritoltetramethacrylate, bisphenol A dimethacrylate, and combinations thereof;(ii) at least one non-silicone hydrophobic vinylic monomer whichcomprises at least one C₁-C₈ alkyl (meth)acrylate, at least one C₅-C₁₆cycloalkyl (meth)acrylate, at least one aryl methacrylate,(meth)acrylonitrile, at least one fluorine-containing acrylic monomer,at least one vinyl alkanoate, at least one vinyloxyalkane, at least onesubstituted or unsubstituted styrene, vinyl toluene, vinyl chloride,vinylidene chloride, 1-butene, or combinations thereof; (iii) at leastone UV-absorbing vinylic monomer; or (iv) combinations thereof.
 10. Themethod of claim 9, wherein the step of actinically curing is carried outby irradiating the circular layer of the first polymerizable fluidcomposition with the visible light at the specified intensity for atleast about 50% of the curing time.
 11. The method of claim 10, whereinsaid at least one first and second polymerizable materials independentof each other comprises at least one UV-absorbing vinylic monomer. 12.The method of claim 11, wherein said at least one photochromic compoundcomprises a naphthopyran, an indeno-fused naphthopyran (i.e.,indeno-naphthopyran), a heterocyclic ring-fused naphthopyrian, abenzopyran, a phenanthropyran, a quinopyran, a quinolinopyran, afluoroanthenopyran, an anthracene-fused pyran, a tetracene-fused pyran,a spiro(benzindoline) naphthopyran, a spiro(indoline)naphthopyran, aspiro(indoline)benzopyran, a spiro(indoline)quinopyran, aspiro(indoline)pyran, a naphthoxazine, a spirobenzopyran, aspirobenzothiopyran, a naphthacenedione, a benzoxazine, a spirooxazine,a naphthoxazine, a spiro(benzindoline)naphthoxazine, aspiro(indoline)naphthoxazine, a spiro(indoline)pyrido-benzoxazine, aspiro(indoline)-benzoxazine, a spiro(benzindoline) benzoxazine, aspiro(benzindoline)pyridobenzoxazine, a spiro(indoline)fluoranthenoxazine, a spiro(indoline)-quinoxazine, aspiropiperidine-naphthopyran, a piro(indoline)pyronobenzoxazinone, abenzospiropyran, a naphtho-spiropyran, aspirobenzoxazine-pyrrolopyridine, a spironaphthoxazine-pyrrolopyrridine,a spiro-oxazepin-benzoxazine, a spiro-oxazepin-naphthoxazine, aspiro(indoline) benzothiazoloxazine, aspiro(indoline)benzopyrroloxazine, a spiro(indoline)quinazolino-oxazine,a spiro(indoline)-anthracenobenzoxazine, a benzofurobenzopyran, abenzothienobenzopyran, a naphthofurobenzopyran, a benzopyrano-fusednaphthopyran, a spiro(isoindoline)-naphthoxazine, aspiro(isoindoline)benzoxazine, or a mixture thereof.
 13. The method ofclaim 12, wherein said at least one photochromic compound ispolymerizable (i.e., comprising an ethylenically-unsaturated group). 14.The method of claim 13, wherein said at least one photochromic compoundis a coupling reaction product of a reactive (meth)acrylamido or(meth)acryloxy monomer having a first reactive functional group and areactive photochromic compound have a second reactive functional groupin the absence or presence of a coupling agent under coupling reaction,wherein the first reactive functional group is selected from the groupconsisting of —COCl, —COBr, —COOH, —NHR_(N2), —NCO, —OH, —CHO,

wherein the second reactive functional group is selected from the groupconsisting of —COOH, —NHR_(N2),

—NCO, —OH, —SH, —CHO,

wherein R₀ is hydrogen or methyl and R_(N2) is hydrogen, a linear orbranched C₁-C₁₅ alkyl, cyclohexyl, cyclopentyl, a substituted orunsubstituted phenyl, or a substituted- or unsubstituted-phenyl-C₁-C₆alkyl.
 15. The method of claim 14, wherein the reactive (meth)acrylamidoor (meth)acryloxy monomer is selected from the group consisting of(meth)acryloyl halides (CH₂═CH—COX or CH₂═CCH₃—COX, X═Cl or Br),N-hydroxysuccinimide ester of (meth)acrylic acid, glycidyl(meth)acrylate, isocyanato-C₂-C₆ alkyl (meth)acrylate, amino-C₂-C₆ alkyl(meth)acrylamide, C₁-C₆ alkylamino-C₂-C₆ alkyl (meth)acrylamide,(meth)acrylic acid, C₂-C₄ alkylacrylic acid (e.g., ethylacrylic acid,propylacrylic acid, butylacrylic acid), N-2-acrylamidoglycolic acid,3-(acryloylxy)propanoic acid, C₂-C₆ hydroxylalkyl (meth)acrylate, C₂-C₆hydroxyalkyl (meth)acrylamide, azlactone-containing vinylic monomers(e.g., 2-vinyl-4,4-dimethyl-1,3-oxazolin-5-one,2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one,2-vinyl-4-methyl-4-ethyl-1,3-oxazolin-5-one,2-isopropenyl-4-methyl-4-butyl-1,3-oxazolin-5-one,2-vinyl-4,4-dibutyl-1,3-oxazolin-5-one,2-isopropenyl-4-methyl-4-dodecyl-1,3-oxazolin-5-one,2-isopropenyl-4,4-diphenyl-1,3-oxazolin-5-one,2-isopropenyl-4,4-pentamethylene-1,3-oxazolin-5-one,2-isopropenyl-4,4-tetramethylene-1,3-oxazolin-5-one,2-vinyl-4,4-diethyl-1,3-oxazolin-5-one,2-vinyl-4-methyl-4-nonyl-1,3-oxazolin-5-one,2-isopropenyl-4-methyl-4-phenyl-1,3-oxazolin-5-one,2-isopropenyl-4-methyl-4-benzyl-1,3-oxazolin-5-one,2-vinyl-4,4-pentamethylene-1,3-oxazolin-5-one, and2-vinyl-4,4-dimethyl-1,3-oxazolin-6-one, with2-vinyl-4,4-dimethyl-1,3-oxazolin-5-one (VDMO) and2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one (IPDMO) as preferredazlactone-containing vinylic monomers), aziridinyl C₁-C₁₂ alkyl(meth)acrylate (e.g., 2-(1-aziridinyl) ethyl (meth)acrylate,3-(1-aziridinyl) propyl (meth)acrylate, 4-(1-aziridinyl) butyl(meth)acrylate, 6-(1-aziridinyl) hexyl (meth)acrylate, or8-(1-aziridinyl) octyl (meth)acrylate), acrolein, methacrolein,crotonaldehyde, and combinations thereof.
 16. The method of claim 15,wherein the reactive photochromic compound comprises3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-hydroxyethoxy-13-phenyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-(2-hydroxycarbonylethyl)carboxyethoxy-13-phenyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-hydroxy-13-phenyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-(2-hydroxycarbonylethyl)carboxy-13-phenyl-3H,13H-indeno[2′,3′:3,4] naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-hydroxy-13-propyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-(2-hydroxycarbonylethyl)carboxy-13-propyl-3H,13H-indeno[2′,3′:3,4]-naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13-(2-hydroxycarbonylethyl)carboxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-7-methoxy-11-phenyl-13-hydroxymethyl-13-methyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-7-methoxy-11-phenyl-13-(2-hydroxycarbonylethyl)carboxymethyl-13-methyl-3H,13H-indeno[2′,3′:3,4]-naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-7-methoxy-11-phenyl-13-hydroxy-13-methyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-7-methoxy-11-phenyl-13-(2-hydroxycarbonylethyl)carboxy-13-methyl-3H,13H-indeno-[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-11-phenyl-13-hydroxy-13-methyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-11-phenyl-13-(2-hydroxycarbonylethyl)carboxy-13-methyl-3H,13H-indeno[2′,3′:3,4]-naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-6,7,10,11-tetramethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-6,7,10,11-tetramethyl-13-(2-hydroxycarbonylethyl)carboxy-13-methyl-3H,13H-indeno[2′,3′:3,4]-naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-6,7-dimethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-11-(4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-6-methoxy-7-(3-hydroxymethylenepiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;3,3-di(4-methoxyphenyl)-6-methoxy-7-(3-(2-hydroxycarbonylethyl)-carboxymethylenepiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;3,3-di(4-methoxyphenyl)-6,7-dimethoxy-13-hydroxy-13-butyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-6,11,13-trimethyl-13-(2-(2-hydroxyethoxy)-ethoxy)-indeno[2,1-f]naptho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-6,11,13-trimethyl-13-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)-indeno[2,1-f]naptho[1,2-b]pyran;3,3-diphenyl-13-hydroxy-13-(2-oxo-2-ethoxyethyl)-1H-indeno[2,1-f]naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-6,11-dimethyl-13-hydroxy-13-(2-oxo-2-ethoxyethyl)-1H-indeno[2,1-f]naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-6,11-dimethyl-13-butyl-13-hydroxy-indeno[2,1-f]naphtho[1,2-b]pyran;3,3-bis(4-hydroxyphenyl)-7-methoxy-11-phenyl-13,13-diethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-hydroxyphenyl)-7-methoxy-11-phenyl-13,13-dipropyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-hydroxyphenyl)-7-methoxy-11-phenyl-13-carbomethoxy-13-methyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-diphenyl-6,7-dimethoxy-13-methyl-13-methyl-13-hydroxyethoxy-ethoxyethoxy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-diphenyl-6,7,10,11-tetramethoxy-13-ethyl-13-methyl-13-hydroxyethoxyethoxy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;6,7-dimthoxy-2,2-diphenyl-13-hydroxy-13-butyl-2H,13H-indeno[1′,2′:4,3]naphtho[1,2-b]pyran;6,7-dimthoxy-2,2-diphenyl-13-hydroxy-13-methyl-2H,13H-indeno[1′,2′:4,3]naphtho[1,2-b]pyran;6,7-dimthoxy-2,2-diphenyl-13-hydroxy-2H,13H-indeno[1′,2′:4,3]naphtho[1,2-b]pyran;3-(4-allyloxyphenyl)-3-(4-morpholinophenyl)-7-methoxy-11-phenyl-13,13-dimethy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-(4-fluorophenyl)-3-(4-butoxyphenyl)-10-(piperazin-1-yl)-6-trifluoromethyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3:4]naphtho[1,2-b]pyran;3-(4-fluorophenyl)-3-(4-butoxyphenyl)-10-(4-hydroxybenzamido)-6-trifluoromethyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3:4]naphtho[1,2-b]pyran;3-(4-fluorophenyl)-3-(4-butoxyphenyl)-10-vinyl-6-trifluoromethyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3:4]naphtho[1,2-b]pyran;3-(4-fluorophenyl)-3-(4-butoxyphenyl)-10-(carboxylicacid)-6-trifluoromethyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3:4]naphtho[1,2-b]pyran;3-(4-fluorophenyl)-3-(4-methoxyphenyl)-6-methoxy-7-(4-hydroxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-(4-fluorophenyl)-3-(4-methoxyphenyl)-6-methoxy-7-(4-(2-hydroxycarbonylethyl)carboxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-(4-fluorophenyl)-3-(4-morpholinophenyl)-6-methoxy-7-(4-hydroxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;3-(4-fluorophenyl)-3-(4-morpholinophenyl)-6-methoxy-7-(4-(2-hydroxycarbonylethyl)carboxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;3-(4-hydroxyethoxyphenyl)-3-(4-methoxyphenyl)-11-(4-(N,N-dimethylamino)phenyl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-(2,4-dimethoxyphenyl)-phenyl-6,11-dimethoxy-13-methyl-13-methyl-13-hydroxyethoxyethoxyethoxy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-(3-methyl-4-methoxyphenyl)-13-hydroxy-indeno[2,1-f]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-6,7,10,11-tetramethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-6,7,10,11-tetramethoxy-13-hydroxy-13-butyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-6,7-dimethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-6,7-dimethoxy-13-hydroxy-13-methyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-13-oxo-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-phenyl-6-methoxy-7-mprphlino-13-methyl-13-methyl-13-hydroxyethoxyethoxyethoxy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-phenyl-6,11-dimethoxy-13-methyl-13-methyl-13-hydroxyethoxy-ethoxy-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;2-(4-methoxyphenyl)-2-(4-morpholinophenyl)-5-hydroxy-6-carboethoxy-2H-naphtho[1,2-b]pyran;3-(4-morpholinophenyl)-3-phenyl-6,7-dimethoxy-13-hydroxy-13-ethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3-(4-morpholinophenyl)-3-phenyl-6,7-dimethoxy-13-hydroxy-13-butyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3-(4-morpholinophenyl)-3-phenyl-6,7-dimethoxy-13-oxo-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;3-phenyl-3-(4-hydroxyethoxyphenyl)-6-methoxy-7-morpholino-13,13-dimethyl-3H,13H-indeno-[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-(2-hydroxycarbonylethyl)carboxyethoxy-phenyl)-6-methoxy-7-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-(2-hydroxyethoxy)phenyl)-6-methoxy-7-piperidino-13,13-dimethy-3H,13H-indene[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-(2-(2-hydroxycarbonylethyl)-carboxyethoxy)phenyl)-6-methoxy-7-piperidino-13,13-dimethy-3H,13H-indene[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-hydroxyphenyl)-6,7-dimethoxy-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-hydroxyethoxy)phenyl)-6,7-dimethoxy-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]-naphtho[1,2-b]pyran;3-phenyl-3-(4-(2-hydroxycarbonylethyl)carboxyethoxy)phenyl)-6,7-dimethoxy-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-(2-hydroxycarbonylethyl)carboxy-phenyl)-6,7-dimethoxy-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-(4-(2-(2-hydroxycarbonylethyl)-carboxyethyl)piperazin-1-yl)phenyl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;3-phenyl-3-(4-methoxyphenyl)-6-methoxy-7-piperazinyl-13,13-dimethyl-3H,13H-indene[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-methoxyphenyl)-6-methoxy-7-(3-hydroxymethylenepiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3″:3.4]naphtho[1.2-b]pyran;3-phenyl-3-(4-methoxyphenyl)-6-methoxy-7-(3-(2-hydroxycarbonylethyl)carboxymethylenepiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3″:3.4]naphtho[1.2-b]pyran;3-phenyl-3-(4-methoxyphenyl)-6-methoxy-7-(4-hydroxypipendin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;3-phenyl-3-(4-methoxyphenyl)-6-methoxy-7-(4-(2-hydroxycarbonylethyl)-carboxypipendin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-(4-methoxyphenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-hydroxy-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-(4-methoxyphenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(2-hydroxy-2-methyl-3-butyn-4-yl)-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-(3-hydroxymethylene-piperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-(3-(2-hydroxycarbonyl-ethyl)carboxymethylene-piperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3.4]-naphtho[1,2-b]pyran;3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-(3-(2-hydroxycarbonylethyl)carboxymethylene-piperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-(4-hydroxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-(4-(2-hydroxycarbonylethyl)-carboxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;3-phenyl-3-(4-morpholinophenyl)-6-methoxy-7-piperazinyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;3-phenyl-3-(4-morpholinophenyl)-6,11-dimethyl-13-hydroxy-13-(1-oxo-methoxyprop-2-yl)-1H-indeno[2,1-f]naphtho[1,2-b]pyran;3-phenyl-3-(4-(4-phenylpiperazino)-phenyl)-6-methoxy-7-(4-hydroxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;3-phenyl-3-(4-(4-phenylpiperazino)phenyl)-6-methoxy-7-(4-(2-hydroxycarbonylethyl)carboxypiperidin-1-yl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1.2-b]pyran;3-phenyl-3-(4-piperazinylphenyl)-6,11-dimethoxy-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;3-phenyl-3-(4-piperazinylphenyl)-6-methoxy-7-piperidinyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-(3-methylpiperazin-1-yl)phenyl)-6-methoxy-7-(decahydroisoquinolin-2-yl)-11-tert-butyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-16-(ethoxycarnobyl)methyl-16-hydroxy-3,16-dihydrobenzofuro-[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3-phenyl-3-(4-methoxyphenyl)-16-(ethoxycarnobyl)-methyl-16-hydroxy-3,16-dihydrobenzofuro[2″,3″:6′,7′]indeno-[3′,2′:4,3]naphtho[1,2-b]pyran;3-phenyl-3-(4-morpholinophenyl)-16-(ethoxycarnobyl)-methyl-16-hydroxy-3,16-dihydrobenzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-dihydro-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran; 3,3-di(4-methoxyphenyl)-16-hydroxy-16H-benzofuro[2″,3″:6,7]indeno [3′,2′:4,3]naphtho-[1,2-b]pyran;3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2″,3″:6,7]-indeno[3′,2′:4,3]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-(2,3-diydrobenzofur-5-yl)-13-hydroxy-13-methyl-indeno[2,1-f]naphtho[1,2-b]pyran;3-(4-methoxyphenyl)-3-(2,3-dihydrobenzofur-5-yl)-6,11-difluoro-13-hydroxy-13-(1-oxo-methoxyprop-2-yl)-1H-indeno[2,1-f]naphtho[1,2-b]pyran,or a mixture thereof.
 17. The method of claim 15, wherein the reactivephotochromic compound is2,2-di(4-fluorophenyl)-5-hydroxycarbonyl-6-phenyl-9-methoxy-2H-naphtho[1,2-b]pyran;2,2-bis(4-methylphenyl)-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;2,2-bis(4-methoxy-phenyl)-5-methoxycarbonyl-6-hydroxy-[2H]-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-methoxyethoxycarbonyl-6-methyl-8-vinyl-2H-naphtho[1,2-b]pyran;2,2-bis(4-methoxy-phenyl)-5-methoxyethoxycarbonyl-6-methyl-8-hydroxycarbonyl-2H-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-(2-hydroxyethoxy)ethoxy-[2H]-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-phenyl-9-(2-hydroxyethoxy)-[2H]-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-methoxy-carbonyl-6-(4-(2-hydroxy-ethoxy)phenyl)-[2H]-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-diphenylmethylol-6-hydroxy-2H-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-diphenylmethylol-6-methoxy-2H-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-(2-hydroxyethoxylcarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-(2-(2-hydroxyethoxy)-ethoxycarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-(2-(2-(2-hydroxyethoxy)ethoxy)-ethoxycarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-(2-(2-(2-(2-hydroxyethoxy)ethoxy)-ethoxy)-ethoxycarbonyl)-6-phenyl-[2H]-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-hydroxymethyl-6-methyl-9-methoxy-2H-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-hydroxymethyl-6-phenyl-2H-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-hydroxymethyl-6-methoxy-2H-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-(3-aminophenyl)-2H-naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-2,5,7-trihydro-7-methylidine-5-oxo-furo-[3′,4′:3,4]naphtho[1,2-b]pyran;2,2-bis(4-methoxyphenyl)-5-phenylthio-6-hydroxy-2H-naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-13-hydroxy-13-methyl-indeno[2,1-f]naphtho[1,2-b]pyran;3,3-di(4-methoxyphenyl)-9-methoxycarbonyl-8-(2-hydroxyethoxy)ethoxy-[3H]-naptho[1,2-b]pyran;2,2-diphenyl-5-hydroxycarbonyl-9-methoxy-2H-naphtho[1,2-b]pyran;2,2-diphenyl-5-hydroxycarbonyl-8,9-dimethoxy-2H-naphtho[1,2-b]pyran;2,2-diphenyl-5-hydroxy-6-carboethoxy-2H-naphtho[1,2-b]pyran;2,2-diphenyl-5-hydroxy-6-morpholinocarbonyl-2H-naphtho[1,2-b]pyran;2,2-diphenyl-5-hydroxy-6-carboethoxy-2H-naphtho[1,2-b]pyran;2,2-diphenyl-5-hydroxy-6-carbomethoxy-9-methoxy-2H-naphtho[1,2-b]pyran;2,2-diphenyl-5-hydroxy-6-morpholino-carbonyl-2H-naphtho[1,2-b]pyran;2,2-diphenyl-5-methylol-6-(3-dimethylaminopropyl)-methylamino-2H-naphtho[1,2-b]pyran;2,2-diphenyl-2,5,7-trihydro-7-methyliden-5-oxofuro-[3′,4′:3,4]naphtho[1,2-b]pyran;2,2-spiroadamantylene-5-phenylthio-6-hydroxy-2H-naphtho[1,2-b]pyran;2,2-diphenyl)-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;2,2-spiro-admamtylene-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran,3,3-diphenyl-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;2,2,5-triphenyl-6-carboethoxy-2H-naphtho[1,2-b]pyran;2,2,6-triphenyl-5-(2-(2-(2-(2-hydroxyethoxy)ethoxy)-ethoxy)ethoxy)carbonyl-[2H]-naphtho[1,2-b]pyran;2,2,6-triphenyl-5-(2-(2-(2-oxiran-2-ylmethoxy)ethoxy)ethoxy)-ethoxycarbonyl)-[2H]-naphtho[1,2-b]pyran;2-(4-methoxyphenyl)-2-(4-morpholinophenyl)-5-hydroxy-6-carboethoxy-2H-naphtho[1,2-b]pyran;2-(4-methoxy-phenyl)-2-tert-butyl-5-methoxy-carbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;2-(4-methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;2-(4-(2-(2-hydroxyethoxy)ethoxy)-ethoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-methyl-9-methoxy-[2H]-naphtho[1,2-b]pyran;2-(4-(2-(2-hydroxyethoxy)ethoxy)phenyl)-2-phenyl-5-methoxycarbonyl-6-(2-(2-methylprop-2-enoxyloxy)ethoxy)-[2H]-naphtho[1,2-b]pyran;3-(4-(2-(2-hydroxyethoxy)-ethoxy)ethoxyphenyl)-3-phenyl-9-methoxycarbonyl-8-methoxy-[3H]-naptho[1,2-b]pyran;2-(4-morpholinophenyl)-2-phenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;2-(9-ethylcarbazol-2-yl)-2-phenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;2-(9-phenylcarbazol-2-yl)-2-phenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;2-(4-dimethylaminophenyl)-2-phenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;3-(2-flurophenyl)-3-(4-methoxyphenyl-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;3-(2-flurophenyl)-3-(4-methoxyphenyl-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;3-(2,4,6-triflurophenyl)-3-(2,4,6-trimethoxy-1-naphthyl)-8-acetyl-9-carboniloyl-3H-naphtho[2,1-b]pyran;3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-6-methoxy-12-hydroxymethyl-11-phenyl-3H-phenanthro[1,2-b]pyran;5,5-bis(4-methoxyphenyl)-8-methylol-5H-fluorantheno[3,2-b]pyran; or amixture thereof.
 18. The method of claim 15, wherein the reactivephotochromic compound is1-hydroxy-ethyl-3,3-dimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1-hydroxypropyl-3,3-dimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1-aminoethyl-3,3-dimethyl-5-chlorospiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1-hydroxyethyl-3,3-dimethyl-8′-methoxyspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1-(p-vinylphenyl)-3,3-dimethyl-5,6-dichlorospiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1,3,3-trimethyl-9′-hydroxy-spiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1,3,3-trimethyl-5′-hydroxymethylspiro-[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1,3,3-trimethyl-9′-aminospiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1,3,3-trimethyl-5-chloro-8′-hydroxyspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1-benzyl-3,3-dimethyl-9′-vinylbenzoyloxyspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1-benzyl-3,3-dimethyl-5′-hydroxymethylpiperidinospiro-naphthooxazine;1,3,3-trimethyl-9′-hydroxyspiro[indoline-2,3′-[3H]-pyrido-[2,1-b][1,4]benzooxazine];5-hydroxy-6′-cyano-1,3,3-trimethyl-spiro-[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];5-hydroxy-6′-phenylsulfonyl-1,3,3-trimethyl-spiro-[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];5′formyl-1,3,3-trimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine;1,3-dihydro-6′-piperazino-1,3,3-trimethyl spiro [2Hindole-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine;1,3-dihydro-6′-(4-hydroxyethyl)piperazino-1,3,3-trimethyl spiro [2Hindole-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine;1,3-dihydro-9′-hydroxy-1,3,3-trimethyl spiro 92Hindole-2,3′-[3H]-naphtho[2,1-b][1,4] oxazine;1,3,3,4,5-pentamethyl-9′-methoxycarbonyl-8′-hydroxy-spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine;1,3,3,5,6-pentamethyl-9′-methoxycarbonyl-8′-hydroxy-spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine;1-propyl-3,3,4,5-tetramethyl-9′-methoxycarbonyl-8′-hydroxy-spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine;1-propyl-3,3,5,6-tetramethyl-9′-methoxycarbonyl-8′-hydroxy-spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine;1-methoxyethyl-3,3-dimethyl-9′-allyloxycarbonyl-8′-chloroactoxy-spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine;1-allyl-3,3-spirocyclohexyl-9′-benzyloxycarbonyl-8′-chloroactoxy-spiro[indoline-2,3′-[3H]naphth-[2,1-b][1,4]oxazine;5-amino-1,3,3-trimethyl-spiro[indoline-2,3′-[3H]-pyrido[3,4-f][1,4]-benzoxazine;6-hydroxy-1′,3′,3′,4′,5′-pentamethylspiro[2H-1,4-benzoxazine-2,2′-indoline];6-hydroxy-1′,3′,3′,5′,6′-pentamethylspiro[2H-1,4-benzoxazine-2,2′-indoline];5,7-dimethoxy-1′-hydroxy-carbonylethyl-3′,3′-dimethylspiro[2H-1,4-bezoxazine-2,2′-indoline];7-methoxy-1′-hydroxy-ethyl-3′,3′-dimethylspiro[2H-1,4-bezoxazine-2,2′-indoline];9′-hydroxy-1-methyl-spiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];5-chloro-9′-hydroxy-1-methylspiro-[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];8′-hydroxy-1-methylspiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];8′-hydroxy-5-methoxy-1-methylspiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];8′-hydroxy-1,4,5-trimethylspiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];9′-hydroxy-1-isopropylspiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];9′-hydroxy-1-hexadecyl-spiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];9′-hydroxy-1-octadecylspiro[indoline-2,3′-(3H)-naphtho(2,1-b)-1,4-oxazine];1,1″-(1,5-pentanediyl)bis[3,3-dimethyl]-9′-hydroxy-spiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine]; 1,1″-[1,4-phenylenebis(methylene)]bis[3,3-dimethyl]-5′-hydroxymethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1,1″-(1,4-butanediyl)bis[5,6-dichloro-3,3-dimethyl]-8′-hydroxy-spiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine]; 1,3,3-trimethyl-9′-hydroxypiperidino-spironaphthooxazine;3-carboxyethyl-1,1-dimethyl-9′-methoxy-spiro[benz[e]-indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1-carboxyethyl-3,3-dimethyl-9′-methoxyspiro[benz[g]-indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];1,1-dimethyl-3-hydroxyethyl-9′-methoxy-spiro[benz[e]-indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];3,3-dimethyl-1-hydroxyethyl-9′-methoxyspiro[benz[g]-indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];3-carboxyethyl-1,1-dimethyl-9′-methoxyspiro[benz[e]-indoline-2,3′-[3H]-pyrido[2,1-b][1,4]benzoxazine];1-carboxyethyl-3,3-dimethyl-9′-methoxyspiro[benz[g]-indoline-2,3′-[3H]-pyrido[2,1-b][1,4]benzoxazine];1,1-dimethyl-3-hydroxyethyl-9′-methoxyspiro[benz[e]-indoline-2,3′-[3H]-pyrido[2,1-b][1,4]benzoxazine];3,3-dimethyl-1-hydroxyethyl-9′-methoxyspiro[benz[g]-indoline-2,3′-[3H]-pyrido[2,1-b][1,4]benzoxazine];5-amino-5′-(2-benzthiazolyl)-1,3,3-trimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];5-amino-5′-(5′-(2-hydroxyphenyl)-2-oxadiazolyl)-1-isopropyl-3,3-dimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];5-amino-5′-(5′-phenyl-2-oxadiazolyl)-1,3,3-trimethylspiro[indoline-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine];or a mixture thereof.
 19. The method of claim 15, wherein the reactivephotochromic compound is3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-hydroxyethoxy-13-phenyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-(2-hydroxycarbonylethyl)carboxyethoxy-13-phenyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-hydroxy-13-phenyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran; or a mixture thereof.
 20. The method ofclaim 15, wherein said at least one first and second polymerizablematerials independent of each other comprises at least one polymerizableUV/HEVL-absorbing compound.
 21. The method of claim 15, wherein said atleast one visible light free radical initiator comprises abenzoylphosphine initiator and/or an acylgermanium photoinitiator. 22.The method of claim 21, wherein the visible light is a visible light ina region of from 420 nm to 500 nm.